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class="vector-toc-numb">2</span> <span>Triflate salts</span> </div> </a> <ul id="toc-Triflate_salts-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" 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mw-first-heading"><span class="mw-page-title-main">Triflate</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. 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href="https://ca.wikipedia.org/wiki/Triflat" title="Triflat – Catalan" lang="ca" hreflang="ca" data-title="Triflat" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Trifl%C3%A1t" title="Triflát – Czech" lang="cs" hreflang="cs" data-title="Triflát" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Triflato" title="Triflato – Spanish" lang="es" hreflang="es" data-title="Triflato" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%AA%D8%B1%DB%8C%E2%80%8C%D9%81%D9%84%D8%A7%D8%AA" title="تری‌فلات – Persian" lang="fa" hreflang="fa" data-title="تری‌فلات" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Triflate" title="Triflate – French" lang="fr" hreflang="fr" data-title="Triflate" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%8A%B8%EB%9D%BC%EC%9D%B4%ED%94%8C%EB%A0%88%EC%9D%B4%ED%8A%B8" title="트라이플레이트 – Korean" lang="ko" hreflang="ko" data-title="트라이플레이트" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Triflato" title="Triflato – Italian" lang="it" hreflang="it" data-title="Triflato" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Triflat" title="Triflat – Malay" lang="ms" hreflang="ms" data-title="Triflat" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Triflylgroep" title="Triflylgroep – Dutch" lang="nl" hreflang="nl" data-title="Triflylgroep" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a 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Việt</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E4%B8%89%E6%B0%9F%E7%94%B2%E7%A3%BA%E9%85%B8%E9%85%AF" title="三氟甲磺酸酯 – Chinese" lang="zh" hreflang="zh" data-title="三氟甲磺酸酯" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q2462024#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li 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class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical group (–OSO2CF3) or anion (charge –1)</div> <p class="mw-empty-elt"> </p> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Triflate.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7d/Triflate.png/150px-Triflate.png" decoding="async" width="150" height="138" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7d/Triflate.png/225px-Triflate.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7d/Triflate.png/300px-Triflate.png 2x" data-file-width="923" data-file-height="850" /></a><figcaption>Triflate group</figcaption></figure> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Triflate-anion.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Triflate-anion.png/150px-Triflate-anion.png" decoding="async" width="150" height="118" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Triflate-anion.png/225px-Triflate-anion.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/93/Triflate-anion.png/300px-Triflate-anion.png 2x" data-file-width="374" data-file-height="294" /></a><figcaption>Triflate <a href="/wiki/Anion" class="mw-redirect" title="Anion">anion</a></figcaption></figure> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, <b>triflate</b> (<a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">systematic name</a>: <b>trifluoromethanesulfonate</b>), is a <a href="/wiki/Functional_group" title="Functional group">functional group</a> with the <a href="/wiki/Chemical_formula" title="Chemical formula">formula</a> <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">R−OSO<sub class="template-chem2-sub">2</sub>CF<sub class="template-chem2-sub">3</sub></span> and <a href="/wiki/Chemical_structure" title="Chemical structure">structure</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−O−S(=O)<sub class="template-chem2-sub">2</sub>−CF<sub class="template-chem2-sub">3</sub></span>. The triflate group is often represented by <b><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−OTf</span></b>, as opposed to −Tf, which is the <a href="/wiki/Trifluoromethylsulfonyl" class="mw-redirect" title="Trifluoromethylsulfonyl">triflyl group</a>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−SO<sub class="template-chem2-sub">2</sub>CF<sub class="template-chem2-sub">3</sub></span>. For example, <a href="/wiki/Butyl_group" title="Butyl group"><i>n</i>-butyl</a> triflate can be written as <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>OTf</span>. </p><p>The corresponding triflate <a href="/wiki/Ion" title="Ion">anion</a>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CF<sub class="template-chem2-sub">3</sub>SO<span class="template-chem2-su"><span>−</span><span>3</span></span></span>, is an extremely stable <a href="/wiki/Polyatomic_ion" title="Polyatomic ion">polyatomic ion</a>; this comes from the fact that <a href="/wiki/Triflic_acid" title="Triflic acid">triflic acid</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CF<sub class="template-chem2-sub">3</sub>SO<sub class="template-chem2-sub">3</sub>H</span>) is a <a href="/wiki/Superacid" title="Superacid">superacid</a>; i.e. it is more acidic than pure <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a>, already one of the strongest <a href="/wiki/Acid" title="Acid">acids</a> known. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Triflate&action=edit&section=1" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A triflate group is an excellent <a href="/wiki/Leaving_group" title="Leaving group">leaving group</a> used in certain <a href="/wiki/Organic_reactions" class="mw-redirect" title="Organic reactions">organic reactions</a> such as <a href="/wiki/Nucleophilic_substitution" title="Nucleophilic substitution">nucleophilic substitution</a>, <a href="/wiki/Suzuki_coupling" class="mw-redirect" title="Suzuki coupling">Suzuki couplings</a> and <a href="/wiki/Heck_reaction" title="Heck reaction">Heck reactions</a>. Since alkyl triflates are extremely reactive in <a href="/wiki/SN2_reaction" title="SN2 reaction">S<sub>N</sub>2 reactions</a>, they must be stored in conditions free of <a href="/wiki/Nucleophile" title="Nucleophile">nucleophiles</a> (such as <a href="/wiki/Water" title="Water">water</a>). The anion owes its stability to <a href="/wiki/Resonance_stabilization" class="mw-redirect" title="Resonance stabilization">resonance stabilization</a> which causes the negative charge to be spread symmetrically over the three oxygen atoms. An additional stabilization is achieved by the <a href="/wiki/Trifluoromethyl" class="mw-redirect" title="Trifluoromethyl">trifluoromethyl</a> group, which acts as a strong <a href="/wiki/Electron-withdrawing_group" title="Electron-withdrawing group">electron-withdrawing group</a> using the sulfur atom as a bridge. </p><p>Triflates have also been applied as ligands for group <a href="/wiki/Group_11_element" title="Group 11 element">11</a> and <a href="/wiki/Group_13_element" class="mw-redirect" title="Group 13 element">13</a> metals along with <a href="/wiki/Lanthanide" title="Lanthanide">lanthanides</a>. </p><p><a href="/wiki/Lithium_triflate" title="Lithium triflate">Lithium triflates</a> are used in some <a href="/wiki/Lithium_ion_batteries" class="mw-redirect" title="Lithium ion batteries">lithium ion batteries</a> as a component of the <a href="/wiki/Electrolyte" title="Electrolyte">electrolyte</a>. </p><p>A mild <b>triflating reagent</b> is phenyl triflimide or <a href="/wiki/Bis(trifluoromethanesulfonyl)aniline" title="Bis(trifluoromethanesulfonyl)aniline"><i>N</i>,<i>N</i>-bis(trifluoromethanesulfonyl)aniline</a>, where the by-product is [CF<sub>3</sub>SO<sub>2</sub>N−Ph]<sup>−</sup>. </p> <div class="mw-heading mw-heading2"><h2 id="Triflate_salts">Triflate salts</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Triflate&action=edit&section=2" title="Edit section: Triflate salts"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Triflate <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salts</a> are thermally very stable with melting points up to 350 °C for <a href="/wiki/Sodium" title="Sodium">sodium</a>, <a href="/wiki/Boron" title="Boron">boron</a> and <a href="/wiki/Silver" title="Silver">silver</a> salts especially in water-free form. They can be obtained directly from triflic acid and the metal hydroxide or metal carbonate in water. Alternatively, they can be obtained from reacting metal chlorides with neat triflic acid or <a href="/wiki/Silver_triflate" class="mw-redirect" title="Silver triflate">silver triflate</a>, or from reacting <a href="/w/index.php?title=Barium_triflate&action=edit&redlink=1" class="new" title="Barium triflate (page does not exist)">barium triflate</a> with metal sulfates in water:<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p><span class="mwe-math-element"><span class="mwe-math-mathml-display mwe-math-mathml-a11y" style="display: none;"><math display="block" xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\begin{aligned}{\ce {MCl}}_{n}+n\,{\ce {HOTf}}&\longrightarrow {\ce {M(OTf)}}_{n}+n\,{\ce {HCl}}\\{\ce {MCl}}_{n}+n\,{\ce {AgOTf}}&\longrightarrow {\ce {M(OTf)}}_{n}+n\,{\ce {AgCl \, v}}\\{\ce {M(SO4)}}_{n}+n\,{\ce {Ba(OTf)2}}&\longrightarrow {\ce {M(OTf)}}_{2n}+n\,{\ce {BaSO4 v}}\end{aligned}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mtable columnalign="right left right left right left right left right left right left" rowspacing="3pt" columnspacing="0em 2em 0em 2em 0em 2em 0em 2em 0em 2em 0em" displaystyle="true"> <mtr> <mtd> <msub> <mrow class="MJX-TeXAtom-ORD"> <mtext>MCl</mtext> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mi>n</mi> </mrow> </msub> <mo>+</mo> <mi>n</mi> <mspace width="thinmathspace" /> <mrow class="MJX-TeXAtom-ORD"> <mtext>HOTf</mtext> </mrow> </mtd> <mtd> <mi></mi> <mo stretchy="false">⟶</mo> <msub> <mrow class="MJX-TeXAtom-ORD"> <mtext>M</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>OTf</mtext> <mo stretchy="false">)</mo> </mrow> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mi>n</mi> </mrow> </msub> <mo>+</mo> <mi>n</mi> <mspace width="thinmathspace" /> <mrow class="MJX-TeXAtom-ORD"> <mtext>HCl</mtext> </mrow> </mtd> </mtr> <mtr> <mtd> <msub> <mrow class="MJX-TeXAtom-ORD"> <mtext>MCl</mtext> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mi>n</mi> </mrow> </msub> <mo>+</mo> <mi>n</mi> <mspace width="thinmathspace" /> <mrow class="MJX-TeXAtom-ORD"> <mtext>AgOTf</mtext> </mrow> </mtd> <mtd> <mi></mi> <mo stretchy="false">⟶</mo> <msub> <mrow class="MJX-TeXAtom-ORD"> <mtext>M</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>OTf</mtext> <mo stretchy="false">)</mo> </mrow> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mi>n</mi> </mrow> </msub> <mo>+</mo> <mi>n</mi> <mspace width="thinmathspace" /> <mrow class="MJX-TeXAtom-ORD"> <mtext>AgCl</mtext> <mspace width="thinmathspace" /> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">↓</mo> </mrow> </mrow> </mtd> </mtr> <mtr> <mtd> <msub> <mrow class="MJX-TeXAtom-ORD"> <mtext>M</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>SO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>4</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mi>n</mi> </mrow> </msub> <mo>+</mo> <mi>n</mi> <mspace width="thinmathspace" /> <mrow class="MJX-TeXAtom-ORD"> <mtext>Ba</mtext> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>OTf</mtext> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> </mtd> <mtd> <mi></mi> <mo stretchy="false">⟶</mo> <msub> <mrow class="MJX-TeXAtom-ORD"> <mtext>M</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>OTf</mtext> <mo stretchy="false">)</mo> </mrow> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> <mi>n</mi> </mrow> </msub> <mo>+</mo> <mi>n</mi> <mspace width="thinmathspace" /> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>BaSO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>4</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">↓</mo> </mrow> </mrow> </mtd> </mtr> </mtable> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\begin{aligned}{\ce {MCl}}_{n}+n\,{\ce {HOTf}}&\longrightarrow {\ce {M(OTf)}}_{n}+n\,{\ce {HCl}}\\{\ce {MCl}}_{n}+n\,{\ce {AgOTf}}&\longrightarrow {\ce {M(OTf)}}_{n}+n\,{\ce {AgCl \, v}}\\{\ce {M(SO4)}}_{n}+n\,{\ce {Ba(OTf)2}}&\longrightarrow {\ce {M(OTf)}}_{2n}+n\,{\ce {BaSO4 v}}\end{aligned}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/4f1c09631c3b85246954ea42c20e735f2c5abd05" class="mwe-math-fallback-image-display mw-invert skin-invert" aria-hidden="true" style="vertical-align: -4.006ex; margin-bottom: -0.332ex; width:52.579ex; height:9.843ex;" alt="{\displaystyle {\begin{aligned}{\ce {MCl}}_{n}+n\,{\ce {HOTf}}&\longrightarrow {\ce {M(OTf)}}_{n}+n\,{\ce {HCl}}\\{\ce {MCl}}_{n}+n\,{\ce {AgOTf}}&\longrightarrow {\ce {M(OTf)}}_{n}+n\,{\ce {AgCl \, v}}\\{\ce {M(SO4)}}_{n}+n\,{\ce {Ba(OTf)2}}&\longrightarrow {\ce {M(OTf)}}_{2n}+n\,{\ce {BaSO4 v}}\end{aligned}}}"></span> </p><p>Metal triflates are used as <a href="/wiki/Lewis_acid" class="mw-redirect" title="Lewis acid">Lewis acid</a> catalysts in <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>. Especially useful are the <a href="/wiki/Lanthanide_triflates" class="mw-redirect" title="Lanthanide triflates">lanthanide triflates</a> of the type <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ln(OTf)<sub class="template-chem2-sub">3</sub></span> (where Ln is a <a href="/wiki/Lanthanoid" class="mw-redirect" title="Lanthanoid">lanthanoid</a>). A related popular catalyst <a href="/wiki/Scandium_triflate" class="mw-redirect" title="Scandium triflate">scandium triflate</a> is used in such reactions as <a href="/wiki/Aldol_reaction" title="Aldol reaction">aldol reactions</a> and <a href="/wiki/Diels%E2%80%93Alder_reaction" title="Diels–Alder reaction">Diels–Alder reactions</a>. An example is the <a href="/wiki/Mukaiyama_aldol_addition" title="Mukaiyama aldol addition">Mukaiyama aldol addition</a> reaction between <a href="/wiki/Benzaldehyde" title="Benzaldehyde">benzaldehyde</a> and the <a href="/wiki/Silyl_enol_ether" title="Silyl enol ether">silyl enol ether</a> of <a href="/wiki/Cyclohexanone" title="Cyclohexanone">cyclohexanone</a> with an 81% <a href="/wiki/Chemical_yield" class="mw-redirect" title="Chemical yield">chemical yield</a>.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> The corresponding reaction with the <a href="/wiki/Yttrium" title="Yttrium">yttrium</a> salt fails: </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:ScOTf3-mediated_aldol_condensation_transp.png" class="mw-file-description" title="Sc(OTf)3-mediated aldol condensation"><img alt="Sc(OTf)3-mediated aldol condensation" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ac/ScOTf3-mediated_aldol_condensation_transp.png/600px-ScOTf3-mediated_aldol_condensation_transp.png" decoding="async" width="600" height="136" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ac/ScOTf3-mediated_aldol_condensation_transp.png/900px-ScOTf3-mediated_aldol_condensation_transp.png 1.5x, //upload.wikimedia.org/wikipedia/commons/a/ac/ScOTf3-mediated_aldol_condensation_transp.png 2x" data-file-width="1100" data-file-height="250" /></a><figcaption><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Sc(OTf)<sub class="template-chem2-sub">3</sub></span>-mediated aldol condensation</figcaption></figure> <p>Triflate is a commonly used <a href="/wiki/Weakly_coordinating_anion" class="mw-redirect" title="Weakly coordinating anion">weakly coordinating anion</a>. </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Ni(OTf)2_scheme.tif" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/47/Ni%28OTf%292_scheme.tif/lossless-page1-332px-Ni%28OTf%292_scheme.tif.png" decoding="async" width="332" height="68" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/47/Ni%28OTf%292_scheme.tif/lossless-page1-498px-Ni%28OTf%292_scheme.tif.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/47/Ni%28OTf%292_scheme.tif/lossless-page1-664px-Ni%28OTf%292_scheme.tif.png 2x" data-file-width="1254" data-file-height="257" /></a><figcaption>Use of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ni(OTf)<sub class="template-chem2-sub">2</sub></span> to facilitate C–H functionalization<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Triflate&action=edit&section=3" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid #aaa;font-size:88%;line-height:1.25em;background-color:var(--background-color-interactive-subtle,#f8f9fa);display:flow-root}.mw-parser-output .side-box-abovebelow,.mw-parser-output .side-box-text{padding:0.25em 0.9em}.mw-parser-output .side-box-image{padding:2px 0 2px 0.9em;text-align:center}.mw-parser-output .side-box-imageright{padding:2px 0.9em 2px 0;text-align:center}@media(min-width:500px){.mw-parser-output .side-box-flex{display:flex;align-items:center}.mw-parser-output .side-box-text{flex:1;min-width:0}}@media(min-width:720px){.mw-parser-output .side-box{width:238px}.mw-parser-output .side-box-right{clear:right;float:right;margin-left:1em}.mw-parser-output .side-box-left{margin-right:1em}}</style><style data-mw-deduplicate="TemplateStyles:r1237033735">@media print{body.ns-0 .mw-parser-output .sistersitebox{display:none!important}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}</style><div class="side-box side-box-right plainlinks sistersitebox"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style> <div class="side-box-flex"> <div class="side-box-image"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/30px-Commons-logo.svg.png" decoding="async" width="30" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/45px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/59px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></span></span></div> <div class="side-box-text plainlist">Wikimedia Commons has media related to <span style="font-weight: bold; font-style: italic;"><a href="https://commons.wikimedia.org/wiki/Category:Triflates" class="extiw" title="commons:Category:Triflates">Triflates</a></span>.</div></div> </div> <ul><li><a href="/wiki/Methyl_triflate" class="mw-redirect" title="Methyl triflate">Methyl triflate</a></li> <li><a href="/wiki/Nonaflate" title="Nonaflate">Nonaflate</a></li> <li><a href="/wiki/Trifluoromethanesulfonic_acid" class="mw-redirect" title="Trifluoromethanesulfonic acid">Trifluoromethanesulfonic acid</a></li> <li><a href="/wiki/Metal_triflimidate" title="Metal triflimidate">Metal triflimidate</a></li> <li><a href="/wiki/Comins%27_reagent" title="Comins' reagent">Comins' reagent</a></li> <li><a href="/wiki/Lithium_triflate" title="Lithium triflate">Lithium triflate</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Triflate&action=edit&section=4" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free 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"Nickel-Catalyzed Direct Alkylation of C–H Bonds in Benzamides and Acrylamides with Functionalized Alkyl Halides via Bidentate-Chelation Assistance". <i>Journal of the American Chemical Society</i>. <b>135</b> (14): 5308–5311. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja401344e">10.1021/ja401344e</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/23495861">23495861</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+American+Chemical+Society&rft.atitle=Nickel-Catalyzed+Direct+Alkylation+of+C%E2%80%93H+Bonds+in+Benzamides+and+Acrylamides+with+Functionalized+Alkyl+Halides+via+Bidentate-Chelation+Assistance&rft.volume=135&rft.issue=14&rft.pages=5308-5311&rft.date=2013-04-10&rft_id=info%3Adoi%2F10.1021%2Fja401344e&rft_id=info%3Apmid%2F23495861&rft.aulast=Aihara&rft.aufirst=Yoshinori&rft.au=Chatani%2C+Naoto&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATriflate" class="Z3988"></span></span> </li> </ol></div></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Triflate&oldid=1242350046">https://en.wikipedia.org/w/index.php?title=Triflate&oldid=1242350046</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Sulfonic_acids" title="Category:Sulfonic acids">Sulfonic acids</a></li><li><a href="/wiki/Category:Sulfonyl_groups" title="Category:Sulfonyl groups">Sulfonyl groups</a></li><li><a href="/wiki/Category:Leaving_groups" title="Category:Leaving groups">Leaving groups</a></li><li><a href="/wiki/Category:Triflates" title="Category:Triflates">Triflates</a></li><li><a href="/wiki/Category:Anions" title="Category:Anions">Anions</a></li><li><a href="/wiki/Category:Trifluoromethyl_compounds" title="Category:Trifluoromethyl compounds">Trifluoromethyl compounds</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden categories: <ul><li><a href="/wiki/Category:Articles_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_is_different_from_Wikidata" title="Category:Short description is different from Wikidata">Short description is different from Wikidata</a></li><li><a href="/wiki/Category:Use_dmy_dates_from_July_2024" title="Category:Use dmy dates from July 2024">Use dmy dates from July 2024</a></li><li><a href="/wiki/Category:Commons_category_link_is_locally_defined" title="Category:Commons category link is locally defined">Commons category link is locally defined</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 26 August 2024, at 11:48<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. 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