Promoting Difficult Carbon-Carbon Couplings: Which Ligand Does Best?
A Pd complex, cis‐[Pd(C6F5)2(THF)2] (1), is proposed as a useful touchstone for direct and simple experimental measurement of the relative ability of ancillary ligands to induce C−C coupling. Interestingly, 1 is also a good alternative to other precatalysts used to produce Pd0L. Complex 1 ranks the...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2016-10, Vol.55 (42), p.13276-13280 |
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| creator | Gioria, Estefanía del Pozo, Juan Martínez-Ilarduya, Jesús M. Espinet, Pablo |
| description | A Pd complex, cis‐[Pd(C6F5)2(THF)2] (1), is proposed as a useful touchstone for direct and simple experimental measurement of the relative ability of ancillary ligands to induce C−C coupling. Interestingly, 1 is also a good alternative to other precatalysts used to produce Pd0L. Complex 1 ranks the coupling ability of some popular ligands in the order PtBu3>o‐TolPEWO‐F≈tBuXPhos>P(C6F5)3≈PhPEWO‐F>P(o‐Tol)3≈THF≈tBuBrettPhos≫Xantphos≈PhPEWO‐H≫PPh3 according to their initial coupling rates, whereas their efficiency, depending on competitive hydrolysis, is ranked tBuXPhos≈PtBu3≈o‐TolPEWO‐F>PhPEWO‐F>P(C6F5)3≫tBuBrettPhos>THF≈P(o‐Tol)3>Xantphos>PhPEWO‐H≫PPh3. This “meter” also detects some other possible virtues or complications of ligands such as tBuXPhos or tBuBrettPhos.
Squeezing cross‐coupling products: Complex cis‐[Pd(C6F5)2(THF)2] was used as a meter to quantify directly the efficiency of ligands to promote reductive elimination in carbon–carbon bond formation. The ligand could be ranked and compared to others. The complex is a good precatalyst for palladium(0) catalytic species PdLn. |
| doi_str_mv | 10.1002/anie.201607089 |
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Squeezing cross‐coupling products: Complex cis‐[Pd(C6F5)2(THF)2] was used as a meter to quantify directly the efficiency of ligands to promote reductive elimination in carbon–carbon bond formation. The ligand could be ranked and compared to others. The complex is a good precatalyst for palladium(0) catalytic species PdLn.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201607089</identifier><identifier>PMID: 27634585</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>Complications ; Couplings ; cross-coupling mechanisms ; homogeneous catalysis ; Hydrolysis ; Ligands ; palladium catalysis ; phosphines ; reductive elimination</subject><ispartof>Angewandte Chemie International Edition, 2016-10, Vol.55 (42), p.13276-13280</ispartof><rights>2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5829-ab9ec94d194c7ae6c16b4c4793b4da17d0819c66047a7fd858eabc879a8b75493</citedby><cites>FETCH-LOGICAL-c5829-ab9ec94d194c7ae6c16b4c4793b4da17d0819c66047a7fd858eabc879a8b75493</cites><orcidid>0000-0001-8649-239X ; 0000-0003-4561-1131 ; 0000-0003-4366-7983</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.201607089$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201607089$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27634585$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Gioria, Estefanía</creatorcontrib><creatorcontrib>del Pozo, Juan</creatorcontrib><creatorcontrib>Martínez-Ilarduya, Jesús M.</creatorcontrib><creatorcontrib>Espinet, Pablo</creatorcontrib><title>Promoting Difficult Carbon-Carbon Couplings: Which Ligand Does Best?</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>A Pd complex, cis‐[Pd(C6F5)2(THF)2] (1), is proposed as a useful touchstone for direct and simple experimental measurement of the relative ability of ancillary ligands to induce C−C coupling. Interestingly, 1 is also a good alternative to other precatalysts used to produce Pd0L. Complex 1 ranks the coupling ability of some popular ligands in the order PtBu3>o‐TolPEWO‐F≈tBuXPhos>P(C6F5)3≈PhPEWO‐F>P(o‐Tol)3≈THF≈tBuBrettPhos≫Xantphos≈PhPEWO‐H≫PPh3 according to their initial coupling rates, whereas their efficiency, depending on competitive hydrolysis, is ranked tBuXPhos≈PtBu3≈o‐TolPEWO‐F>PhPEWO‐F>P(C6F5)3≫tBuBrettPhos>THF≈P(o‐Tol)3>Xantphos>PhPEWO‐H≫PPh3. This “meter” also detects some other possible virtues or complications of ligands such as tBuXPhos or tBuBrettPhos.
Squeezing cross‐coupling products: Complex cis‐[Pd(C6F5)2(THF)2] was used as a meter to quantify directly the efficiency of ligands to promote reductive elimination in carbon–carbon bond formation. The ligand could be ranked and compared to others. The complex is a good precatalyst for palladium(0) catalytic species PdLn.</description><subject>Complications</subject><subject>Couplings</subject><subject>cross-coupling mechanisms</subject><subject>homogeneous catalysis</subject><subject>Hydrolysis</subject><subject>Ligands</subject><subject>palladium catalysis</subject><subject>phosphines</subject><subject>reductive elimination</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqF0c1L5DAYBvAgLuqqV49S8OKlY9J8exHt-AWDCo4IXkKaphrtNGMyZdf_fiN1B_GgpzeH3_Mk5AVgB8ERgrA40J2zowIiBjkUcgVsIFqgHHOOV9OZYJxzQdE6-B3jc_JCQLYG1gvOMKGCboDxTfAzv3DdYzZ2TeNM3y6yUofKd_kwstL38zaBeJjdPznzlE3co-7qbOxtzE5sXBxtgV-NbqPd_pib4O7sdFpe5JPr88vyeJIbKgqZ60paI0mNJDFcW2YQq4ghXOKK1BrxGgokDWOQcM2bWlBhdWUEl1pUnBKJN8H-0DsP_rVPN6uZi8a2re6s76NCAlPMIMI40b0v9Nn3oUuvU0hCRnjBEPxWiYJByXDBkhoNygQfY7CNmgc30-FNIajet6Det6CWW0iB3Y_avprZesn_f3sCcgB_XGvffqhTx1eXp5_L8yHr4sL-XWZ1eFGMY07V_dW5mqILeDt9KJXE_wCcdJ_o</recordid><startdate>20161010</startdate><enddate>20161010</enddate><creator>Gioria, Estefanía</creator><creator>del Pozo, Juan</creator><creator>Martínez-Ilarduya, Jesús M.</creator><creator>Espinet, Pablo</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-8649-239X</orcidid><orcidid>https://orcid.org/0000-0003-4561-1131</orcidid><orcidid>https://orcid.org/0000-0003-4366-7983</orcidid></search><sort><creationdate>20161010</creationdate><title>Promoting Difficult Carbon-Carbon Couplings: Which Ligand Does Best?</title><author>Gioria, Estefanía ; del Pozo, Juan ; Martínez-Ilarduya, Jesús M. ; Espinet, Pablo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5829-ab9ec94d194c7ae6c16b4c4793b4da17d0819c66047a7fd858eabc879a8b75493</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Complications</topic><topic>Couplings</topic><topic>cross-coupling mechanisms</topic><topic>homogeneous catalysis</topic><topic>Hydrolysis</topic><topic>Ligands</topic><topic>palladium catalysis</topic><topic>phosphines</topic><topic>reductive elimination</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gioria, Estefanía</creatorcontrib><creatorcontrib>del Pozo, Juan</creatorcontrib><creatorcontrib>Martínez-Ilarduya, Jesús M.</creatorcontrib><creatorcontrib>Espinet, Pablo</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gioria, Estefanía</au><au>del Pozo, Juan</au><au>Martínez-Ilarduya, Jesús M.</au><au>Espinet, Pablo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Promoting Difficult Carbon-Carbon Couplings: Which Ligand Does Best?</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2016-10-10</date><risdate>2016</risdate><volume>55</volume><issue>42</issue><spage>13276</spage><epage>13280</epage><pages>13276-13280</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>A Pd complex, cis‐[Pd(C6F5)2(THF)2] (1), is proposed as a useful touchstone for direct and simple experimental measurement of the relative ability of ancillary ligands to induce C−C coupling. Interestingly, 1 is also a good alternative to other precatalysts used to produce Pd0L. Complex 1 ranks the coupling ability of some popular ligands in the order PtBu3>o‐TolPEWO‐F≈tBuXPhos>P(C6F5)3≈PhPEWO‐F>P(o‐Tol)3≈THF≈tBuBrettPhos≫Xantphos≈PhPEWO‐H≫PPh3 according to their initial coupling rates, whereas their efficiency, depending on competitive hydrolysis, is ranked tBuXPhos≈PtBu3≈o‐TolPEWO‐F>PhPEWO‐F>P(C6F5)3≫tBuBrettPhos>THF≈P(o‐Tol)3>Xantphos>PhPEWO‐H≫PPh3. This “meter” also detects some other possible virtues or complications of ligands such as tBuXPhos or tBuBrettPhos.
Squeezing cross‐coupling products: Complex cis‐[Pd(C6F5)2(THF)2] was used as a meter to quantify directly the efficiency of ligands to promote reductive elimination in carbon–carbon bond formation. The ligand could be ranked and compared to others. The complex is a good precatalyst for palladium(0) catalytic species PdLn.</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>27634585</pmid><doi>10.1002/anie.201607089</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0001-8649-239X</orcidid><orcidid>https://orcid.org/0000-0003-4561-1131</orcidid><orcidid>https://orcid.org/0000-0003-4366-7983</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Complications Couplings cross-coupling mechanisms homogeneous catalysis Hydrolysis Ligands palladium catalysis phosphines reductive elimination |
| title | Promoting Difficult Carbon-Carbon Couplings: Which Ligand Does Best? |
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