Synthesis of Allylarenes via Catalytic Decarboxylation of Allyl Benzoates
A catalyst system consisting of the palladium(0) complex Pd2(dba)3 and tri(p‐tolyl)phosphine was found to efficiently promote the decarboxylation of allyl benzoates with formation of allylarenes. This catalytic CO activation followed by extrusion of carbon dioxide and CC bond formation represents...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2014-11, Vol.356 (16), p.3302-3306 |
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| container_issue | 16 |
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| container_title | Advanced synthesis & catalysis |
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| creator | Pfister, Kai F. Grünberg, Matthias F. Gooßen, Lukas J. |
| description | A catalyst system consisting of the palladium(0) complex Pd2(dba)3 and tri(p‐tolyl)phosphine was found to efficiently promote the decarboxylation of allyl benzoates with formation of allylarenes. This catalytic CO activation followed by extrusion of carbon dioxide and CC bond formation represents a sustainable alternative to traditional waste‐intensive cross‐couplings. The scope of the transformation includes allyl and cinnamyl esters of various ortho‐substituted benzoic acids. For particularly activated substrates, the palladium catalyst can optionally be replaced by an inexpensive nickel complex. |
| doi_str_mv | 10.1002/adsc.201400624 |
| format | Article |
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This catalytic CO activation followed by extrusion of carbon dioxide and CC bond formation represents a sustainable alternative to traditional waste‐intensive cross‐couplings. The scope of the transformation includes allyl and cinnamyl esters of various ortho‐substituted benzoic acids. For particularly activated substrates, the palladium catalyst can optionally be replaced by an inexpensive nickel complex.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201400624</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>allylation ; Benzoates ; Carbon dioxide ; Catalysis ; Catalysts ; Decarboxylation ; Esters ; homogeneous catalysis ; nickel ; palladium ; Synthesis ; Transformations</subject><ispartof>Advanced synthesis & catalysis, 2014-11, Vol.356 (16), p.3302-3306</ispartof><rights>2014 WILEY‐VCH Verlag GmbH & Co. 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Synth. Catal</addtitle><description>A catalyst system consisting of the palladium(0) complex Pd2(dba)3 and tri(p‐tolyl)phosphine was found to efficiently promote the decarboxylation of allyl benzoates with formation of allylarenes. This catalytic CO activation followed by extrusion of carbon dioxide and CC bond formation represents a sustainable alternative to traditional waste‐intensive cross‐couplings. The scope of the transformation includes allyl and cinnamyl esters of various ortho‐substituted benzoic acids. For particularly activated substrates, the palladium catalyst can optionally be replaced by an inexpensive nickel complex.</description><subject>allylation</subject><subject>Benzoates</subject><subject>Carbon dioxide</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Decarboxylation</subject><subject>Esters</subject><subject>homogeneous catalysis</subject><subject>nickel</subject><subject>palladium</subject><subject>Synthesis</subject><subject>Transformations</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNqFkDFPwzAQRiMEEqWwMmdkSbEdx47HktJStYKhoI6W455FwE2KnULDrydVUMTGdJ90751OXxBcYzTCCJFbtfF6RBCmCDFCT4IBZjiJKGbitM8JOg8uvH9DCPOU80EwXzVl_Qq-8GFlwrG1jVUOSvDhZ6HCTNXKNnWhwwlo5fLq0K7roip7OLyD8rtSNfjL4Mwo6-Hqdw6Dl-n9c_YQLZ9m82y8jDRlMY04iA0mRkH7pspNyjXXaQyYYiEAiRQrbFAcE5RrkaeEMGoSZChPWlJvqI6HwU13d-eqjz34Wm4Lr8FaVUK19xIzSgilgrMWHXWodpX3DozcuWKrXCMxksfO5LEz2XfWCqITvgoLzT-0HE9W2V836tzC13DoXeXeJeMxT-T6cSZndIGma7aQy_gH1cJ_NQ</recordid><startdate>20141103</startdate><enddate>20141103</enddate><creator>Pfister, Kai F.</creator><creator>Grünberg, Matthias F.</creator><creator>Gooßen, Lukas J.</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20141103</creationdate><title>Synthesis of Allylarenes via Catalytic Decarboxylation of Allyl Benzoates</title><author>Pfister, Kai F. ; Grünberg, Matthias F. ; Gooßen, Lukas J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4634-7e9d12fae400abf87c7c83e14199e0981a1f03320bc9b82264f50f47587ccd4c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>allylation</topic><topic>Benzoates</topic><topic>Carbon dioxide</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Decarboxylation</topic><topic>Esters</topic><topic>homogeneous catalysis</topic><topic>nickel</topic><topic>palladium</topic><topic>Synthesis</topic><topic>Transformations</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pfister, Kai F.</creatorcontrib><creatorcontrib>Grünberg, Matthias F.</creatorcontrib><creatorcontrib>Gooßen, Lukas J.</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pfister, Kai F.</au><au>Grünberg, Matthias F.</au><au>Gooßen, Lukas J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Allylarenes via Catalytic Decarboxylation of Allyl Benzoates</atitle><jtitle>Advanced synthesis & catalysis</jtitle><addtitle>Adv. Synth. Catal</addtitle><date>2014-11-03</date><risdate>2014</risdate><volume>356</volume><issue>16</issue><spage>3302</spage><epage>3306</epage><pages>3302-3306</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>A catalyst system consisting of the palladium(0) complex Pd2(dba)3 and tri(p‐tolyl)phosphine was found to efficiently promote the decarboxylation of allyl benzoates with formation of allylarenes. This catalytic CO activation followed by extrusion of carbon dioxide and CC bond formation represents a sustainable alternative to traditional waste‐intensive cross‐couplings. The scope of the transformation includes allyl and cinnamyl esters of various ortho‐substituted benzoic acids. For particularly activated substrates, the palladium catalyst can optionally be replaced by an inexpensive nickel complex.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/adsc.201400624</doi><tpages>5</tpages></addata></record> |
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| subjects | allylation Benzoates Carbon dioxide Catalysis Catalysts Decarboxylation Esters homogeneous catalysis nickel palladium Synthesis Transformations |
| title | Synthesis of Allylarenes via Catalytic Decarboxylation of Allyl Benzoates |
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