Chemoselective Boronic Ester Synthesis by Controlled Speciation
Control of boronic acid solution speciation is presented as a new strategy for the chemoselective synthesis of boronic esters. Manipulation of the solution equilibria within a cross‐coupling milieu enables the formal homologation of aryl and alkenyl boronic acid pinacol esters. The generation of a n...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2014-11, Vol.53 (45), p.12077-12080 |
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| creator | Fyfe, James W. B. Seath, Ciaran P. Watson, Allan J. B. |
| description | Control of boronic acid solution speciation is presented as a new strategy for the chemoselective synthesis of boronic esters. Manipulation of the solution equilibria within a cross‐coupling milieu enables the formal homologation of aryl and alkenyl boronic acid pinacol esters. The generation of a new, reactive boronic ester in the presence of an active palladium catalyst also facilitates streamlined iterative catalytic CC bond formation and provides a method for the controlled oligomerization of sp2‐hybridized boronic esters.
Under control: Controlling boron solution speciation during Suzuki–Miyaura cross‐coupling enables the chemoselective synthesis of functionalized boronic acid pinacol esters. A rapid Suzuki–Miyaura reaction followed by controlled pinacol recycle enables the formal homologation of sp2 boronic acid pinacol esters. The reaction can also be used for controlled oligomerization of sp2‐hybridized boronic esters. MIDA=N‐methyliminodiacetic acid, Pin=pinacol. |
| doi_str_mv | 10.1002/anie.201406714 |
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Under control: Controlling boron solution speciation during Suzuki–Miyaura cross‐coupling enables the chemoselective synthesis of functionalized boronic acid pinacol esters. A rapid Suzuki–Miyaura reaction followed by controlled pinacol recycle enables the formal homologation of sp2 boronic acid pinacol esters. The reaction can also be used for controlled oligomerization of sp2‐hybridized boronic esters. MIDA=N‐methyliminodiacetic acid, Pin=pinacol.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201406714</identifier><identifier>PMID: 25267096</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Active control ; Aromatic compounds ; Bonding ; boron ; Boron Compounds - chemical synthesis ; Boron Compounds - chemistry ; Catalysts ; chemoselectivity ; Communications ; cross-coupling ; Esters ; Esters - chemistry ; Homology ; oligomerization ; palladium ; Polymerization ; Speciation ; Strategy ; Synthesis</subject><ispartof>Angewandte Chemie International Edition, 2014-11, Vol.53 (45), p.12077-12080</ispartof><rights>2014 The Authors. Published by Wiley‐VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.</rights><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.</rights><rights>2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. 2014</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c6424-7967e2621aca00c1a518924cf01abc35bfc6babaa6514479038039265e78203d3</citedby><cites>FETCH-LOGICAL-c6424-7967e2621aca00c1a518924cf01abc35bfc6babaa6514479038039265e78203d3</cites></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.201406714$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201406714$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>230,314,777,781,882,1412,27905,27906,45555,45556</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25267096$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Fyfe, James W. B.</creatorcontrib><creatorcontrib>Seath, Ciaran P.</creatorcontrib><creatorcontrib>Watson, Allan J. B.</creatorcontrib><title>Chemoselective Boronic Ester Synthesis by Controlled Speciation</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>Control of boronic acid solution speciation is presented as a new strategy for the chemoselective synthesis of boronic esters. Manipulation of the solution equilibria within a cross‐coupling milieu enables the formal homologation of aryl and alkenyl boronic acid pinacol esters. The generation of a new, reactive boronic ester in the presence of an active palladium catalyst also facilitates streamlined iterative catalytic CC bond formation and provides a method for the controlled oligomerization of sp2‐hybridized boronic esters.
Under control: Controlling boron solution speciation during Suzuki–Miyaura cross‐coupling enables the chemoselective synthesis of functionalized boronic acid pinacol esters. A rapid Suzuki–Miyaura reaction followed by controlled pinacol recycle enables the formal homologation of sp2 boronic acid pinacol esters. The reaction can also be used for controlled oligomerization of sp2‐hybridized boronic esters. MIDA=N‐methyliminodiacetic acid, Pin=pinacol.</description><subject>Active control</subject><subject>Aromatic compounds</subject><subject>Bonding</subject><subject>boron</subject><subject>Boron Compounds - chemical synthesis</subject><subject>Boron Compounds - chemistry</subject><subject>Catalysts</subject><subject>chemoselectivity</subject><subject>Communications</subject><subject>cross-coupling</subject><subject>Esters</subject><subject>Esters - chemistry</subject><subject>Homology</subject><subject>oligomerization</subject><subject>palladium</subject><subject>Polymerization</subject><subject>Speciation</subject><subject>Strategy</subject><subject>Synthesis</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>WIN</sourceid><sourceid>EIF</sourceid><recordid>eNqFkU1vEzEURS1ERUtg22U1Ehs2k_rbng0ojEKoGgWkFLG0PM4LcZmMU3tSyL_HUUrUsunKlnzu1fM7CJ0TPCQY00vbeRhSTDiWivAX6IwISkqmFHuZ75yxUmlBTtHrlG4zrzWWr9ApFVQqXMkz9LFewTokaMH1_h6KTyGGzrtinHqIxXzX9StIPhXNrqhD18fQtrAo5htw3vY-dG_QydK2Cd4-nAP0_fP4pv5STr9OrurRtHSSU16qSiqgkhLrLMaOWEF0RblbYmIbx0SzdLKxjbVSEM5VhZnGrKJSgNIUswUboA-H3s22WcPCQZ7FtmYT_drGnQnWm6cvnV-Zn-HecIEJy4sYoPcPBTHcbSH1Zu2Tg7a1HYRtMkRhgjVVXD2PSqI1lVLRjL77D70N29jlTewpRUTFsM7U8EC5GFKKsDzOTbDZazR7jeaoMQcuHv_2iP_zloHqAPz2LeyeqTOj2dX4cXl5yPrs-M8xa-MvIxVTwvyYTcy3eT1hN9czM2V_ARsft6U</recordid><startdate>20141103</startdate><enddate>20141103</enddate><creator>Fyfe, James W. B.</creator><creator>Seath, Ciaran P.</creator><creator>Watson, Allan J. B.</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>24P</scope><scope>WIN</scope><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>7TM</scope><scope>K9.</scope><scope>7X8</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>5PM</scope></search><sort><creationdate>20141103</creationdate><title>Chemoselective Boronic Ester Synthesis by Controlled Speciation</title><author>Fyfe, James W. B. ; Seath, Ciaran P. ; Watson, Allan J. B.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c6424-7967e2621aca00c1a518924cf01abc35bfc6babaa6514479038039265e78203d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Active control</topic><topic>Aromatic compounds</topic><topic>Bonding</topic><topic>boron</topic><topic>Boron Compounds - chemical synthesis</topic><topic>Boron Compounds - chemistry</topic><topic>Catalysts</topic><topic>chemoselectivity</topic><topic>Communications</topic><topic>cross-coupling</topic><topic>Esters</topic><topic>Esters - chemistry</topic><topic>Homology</topic><topic>oligomerization</topic><topic>palladium</topic><topic>Polymerization</topic><topic>Speciation</topic><topic>Strategy</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fyfe, James W. 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B.</au><au>Seath, Ciaran P.</au><au>Watson, Allan J. B.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chemoselective Boronic Ester Synthesis by Controlled Speciation</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2014-11-03</date><risdate>2014</risdate><volume>53</volume><issue>45</issue><spage>12077</spage><epage>12080</epage><pages>12077-12080</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>Control of boronic acid solution speciation is presented as a new strategy for the chemoselective synthesis of boronic esters. Manipulation of the solution equilibria within a cross‐coupling milieu enables the formal homologation of aryl and alkenyl boronic acid pinacol esters. The generation of a new, reactive boronic ester in the presence of an active palladium catalyst also facilitates streamlined iterative catalytic CC bond formation and provides a method for the controlled oligomerization of sp2‐hybridized boronic esters.
Under control: Controlling boron solution speciation during Suzuki–Miyaura cross‐coupling enables the chemoselective synthesis of functionalized boronic acid pinacol esters. A rapid Suzuki–Miyaura reaction followed by controlled pinacol recycle enables the formal homologation of sp2 boronic acid pinacol esters. The reaction can also be used for controlled oligomerization of sp2‐hybridized boronic esters. MIDA=N‐methyliminodiacetic acid, Pin=pinacol.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>25267096</pmid><doi>10.1002/anie.201406714</doi><tpages>4</tpages><edition>International ed. in English</edition><oa>free_for_read</oa></addata></record> |
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| subjects | Active control Aromatic compounds Bonding boron Boron Compounds - chemical synthesis Boron Compounds - chemistry Catalysts chemoselectivity Communications cross-coupling Esters Esters - chemistry Homology oligomerization palladium Polymerization Speciation Strategy Synthesis |
| title | Chemoselective Boronic Ester Synthesis by Controlled Speciation |
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