Cross Coupling Reactions of Chiral Secondary Organoboronic Esters With Retention of Configuration

We report the first example of a coupling reaction of chiral secondary boronic esters generated by the hydroboration of vinyl arenes. In order for the reaction to take place in high yields, the use of silver oxide as a base and the presence of at least 8 equiv of triphenyl phosphine per Pd are requi...

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Veröffentlicht in:	Journal of the American Chemical Society 2009-04, Vol.131 (14), p.5024-5025
Hauptverfasser:	Imao, Daisuke, Glasspoole, Ben W, Laberge, Véronique S, Crudden, Cathleen M
Format:	Artikel
Sprache:	eng
Schlagworte:	Boron Compounds - chemical synthesis Boron Compounds - chemistry Catalysis Esters - chemical synthesis Esters - chemistry Organophosphorus Compounds - chemistry Oxides - chemistry Palladium - chemistry Silver Compounds - chemistry Stereoisomerism
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creator	Imao, Daisuke Glasspoole, Ben W Laberge, Véronique S Crudden, Cathleen M
description	We report the first example of a coupling reaction of chiral secondary boronic esters generated by the hydroboration of vinyl arenes. In order for the reaction to take place in high yields, the use of silver oxide as a base and the presence of at least 8 equiv of triphenyl phosphine per Pd are required. The reaction proceeds with >90% retention of configuration in all cases except one. Remarkably, the linear boronate ester does not react under these conditions.
doi_str_mv	10.1021/ja8094075
format	Article
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Am. Chem. Soc</addtitle><description>We report the first example of a coupling reaction of chiral secondary boronic esters generated by the hydroboration of vinyl arenes. In order for the reaction to take place in high yields, the use of silver oxide as a base and the presence of at least 8 equiv of triphenyl phosphine per Pd are required. The reaction proceeds with >90% retention of configuration in all cases except one. Remarkably, the linear boronate ester does not react under these conditions.</description><subject>Boron Compounds - chemical synthesis</subject><subject>Boron Compounds - chemistry</subject><subject>Catalysis</subject><subject>Esters - chemical synthesis</subject><subject>Esters - chemistry</subject><subject>Organophosphorus Compounds - chemistry</subject><subject>Oxides - chemistry</subject><subject>Palladium - chemistry</subject><subject>Silver Compounds - chemistry</subject><subject>Stereoisomerism</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkEtLAzEUhYMotlYX_gHJRsHFaG5mMpMsZagPKBR84HJIM0mbMk1qMrPw33fGFt24upzLdw6cg9AlkDsgFO7XkhORkYIdoTEwShIGND9GY0IITQqepyN0FuO6lxnlcIpGIFICnJIxkmXwMeLSd9vGuiV-1VK11ruIvcHlygbZ4DetvKtl-MbzsJTOL3zwzio8ja0OEX_adtX7Wu0G44_PO2OXXZDD4xydGNlEfXG4E_TxOH0vn5PZ_OmlfJglMoW0TaipQTCji4wCA6NTRoEKUXCpiCyEojyjwiiRS64NVwttmDJAdS5qkmecphN0s8_dBv_V6dhWGxuVbhrptO9ilRdAUpZnPXi7B9VQPWhTbYPd9PUqINWwZ_W7Z89eHUK7xUbXf-RhwB643gNSxWrtu-D6jv8E7QDrqnwl</recordid><startdate>20090415</startdate><enddate>20090415</enddate><creator>Imao, Daisuke</creator><creator>Glasspoole, Ben W</creator><creator>Laberge, Véronique S</creator><creator>Crudden, Cathleen M</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20090415</creationdate><title>Cross Coupling Reactions of Chiral Secondary Organoboronic Esters With Retention of Configuration</title><author>Imao, Daisuke ; Glasspoole, Ben W ; Laberge, Véronique S ; Crudden, Cathleen M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a313t-2fd195fe742151fe352129978ac0a79c28429fc96a8ef8cbef5cf12e69d064823</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Boron Compounds - chemical synthesis</topic><topic>Boron Compounds - chemistry</topic><topic>Catalysis</topic><topic>Esters - chemical synthesis</topic><topic>Esters - chemistry</topic><topic>Organophosphorus Compounds - chemistry</topic><topic>Oxides - chemistry</topic><topic>Palladium - chemistry</topic><topic>Silver Compounds - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Imao, Daisuke</creatorcontrib><creatorcontrib>Glasspoole, Ben W</creatorcontrib><creatorcontrib>Laberge, Véronique S</creatorcontrib><creatorcontrib>Crudden, Cathleen M</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Imao, Daisuke</au><au>Glasspoole, Ben W</au><au>Laberge, Véronique S</au><au>Crudden, Cathleen M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cross Coupling Reactions of Chiral Secondary Organoboronic Esters With Retention of Configuration</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. 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subjects	Boron Compounds - chemical synthesis Boron Compounds - chemistry Catalysis Esters - chemical synthesis Esters - chemistry Organophosphorus Compounds - chemistry Oxides - chemistry Palladium - chemistry Silver Compounds - chemistry Stereoisomerism
title	Cross Coupling Reactions of Chiral Secondary Organoboronic Esters With Retention of Configuration
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