Amide-Controlled Highly Selective Catalytic Borylcupration of Allenes
A novel copper‐catalyzed, highly regio‐ and stereoselective borylcupration of substituted 2,3‐allenamides with bis(pinacolato)diboron producing Z‐β‐borylated β,γ‐unsaturated enoamides has been demonstrated. Due to the unique effect of the amide‐group, perfect regio‐ and stereoselectivity and good to...
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| Veröffentlicht in: | Chemistry : a European journal 2013-05, Vol.19 (22), p.7193-7202 |
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| container_title | Chemistry : a European journal |
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| creator | Yuan, Weiming Zhang, Xue Yu, Yihua Ma, Shengming |
| description | A novel copper‐catalyzed, highly regio‐ and stereoselective borylcupration of substituted 2,3‐allenamides with bis(pinacolato)diboron producing Z‐β‐borylated β,γ‐unsaturated enoamides has been demonstrated. Due to the unique effect of the amide‐group, perfect regio‐ and stereoselectivity and good to excellent yields have been achieved, which were rationalized by a DFT study.
Perfect selection! A copper‐catalyzed, highly regio‐ and stereoselective borylcupration of 2,3‐allenamide with bis(pinacolato)diboron producing Z‐β‐borylated β,γ‐unsaturated amides has been developed (see scheme; L=large, S=small). Due to the unique effect of the amide group, perfect regio‐ and stereoselectivity and good to excellent yields have been achieved. The results have been rationalized by a DFT study. |
| doi_str_mv | 10.1002/chem.201202835 |
| format | Article |
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Perfect selection! A copper‐catalyzed, highly regio‐ and stereoselective borylcupration of 2,3‐allenamide with bis(pinacolato)diboron producing Z‐β‐borylated β,γ‐unsaturated amides has been developed (see scheme; L=large, S=small). Due to the unique effect of the amide group, perfect regio‐ and stereoselectivity and good to excellent yields have been achieved. The results have been rationalized by a DFT study.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201202835</identifier><identifier>PMID: 23559155</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>allenes ; Amides ; Beta ; boron ; Catalysis ; Catalysts ; Chemistry ; copper ; regioselectivity ; Stereoselectivity</subject><ispartof>Chemistry : a European journal, 2013-05, Vol.19 (22), p.7193-7202</ispartof><rights>Copyright © 2013 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5475-2a4955f9553c394ac33d91374f61fc59f2564eb3735031c37a38984547519ced3</citedby><cites>FETCH-LOGICAL-c5475-2a4955f9553c394ac33d91374f61fc59f2564eb3735031c37a38984547519ced3</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%2Fchem.201202835$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201202835$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23559155$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yuan, Weiming</creatorcontrib><creatorcontrib>Zhang, Xue</creatorcontrib><creatorcontrib>Yu, Yihua</creatorcontrib><creatorcontrib>Ma, Shengming</creatorcontrib><title>Amide-Controlled Highly Selective Catalytic Borylcupration of Allenes</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>A novel copper‐catalyzed, highly regio‐ and stereoselective borylcupration of substituted 2,3‐allenamides with bis(pinacolato)diboron producing Z‐β‐borylated β,γ‐unsaturated enoamides has been demonstrated. Due to the unique effect of the amide‐group, perfect regio‐ and stereoselectivity and good to excellent yields have been achieved, which were rationalized by a DFT study.
Perfect selection! A copper‐catalyzed, highly regio‐ and stereoselective borylcupration of 2,3‐allenamide with bis(pinacolato)diboron producing Z‐β‐borylated β,γ‐unsaturated amides has been developed (see scheme; L=large, S=small). Due to the unique effect of the amide group, perfect regio‐ and stereoselectivity and good to excellent yields have been achieved. The results have been rationalized by a DFT study.</description><subject>allenes</subject><subject>Amides</subject><subject>Beta</subject><subject>boron</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Chemistry</subject><subject>copper</subject><subject>regioselectivity</subject><subject>Stereoselectivity</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNqF0c9v2yAcBXBUbWqzrtceJ0u77OIU-IIxx8xKk0n9Ja3VdkMU45UOmwzsbv7v5yhdNPXSA-LyeU-Ch9ApwXOCMT0zD7adU0wopiXwAzQjnJIcRMHfoBmWTOQFB3mE3qX0iDGWBcAhOqLAuSScz9By0bra5lXo-hi8t3W2dj8e_Jh9td6a3j3ZrNK99mPvTPY5xNGbYRN170KXhSZbTJHOpvfobaN9sifP9zG6O1_eVuv84nr1pVpc5IYzwXOqmeS8mQ4YkEwbgFoSEKwpSGO4bCgvmL0HARwDMSA0lLJk2yyRxtZwjD7tejcx_Bps6lXrkrHe686GISkiRImJhBK_ToEDZsCEnOjHF_QxDLGbHrJVlE4QyknNd8rEkFK0jdpE1-o4KoLVdgu13ULtt5gCH55rh_vW1nv-7_MnIHfgt_N2fKVOVevl5f_l-S7rUm__7LM6_lSFAMHVt6uVYuzm6jte3SiAv5H6oY0</recordid><startdate>20130527</startdate><enddate>20130527</enddate><creator>Yuan, Weiming</creator><creator>Zhang, Xue</creator><creator>Yu, Yihua</creator><creator>Ma, Shengming</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>20130527</creationdate><title>Amide-Controlled Highly Selective Catalytic Borylcupration of Allenes</title><author>Yuan, Weiming ; Zhang, Xue ; Yu, Yihua ; Ma, Shengming</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5475-2a4955f9553c394ac33d91374f61fc59f2564eb3735031c37a38984547519ced3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>allenes</topic><topic>Amides</topic><topic>Beta</topic><topic>boron</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Chemistry</topic><topic>copper</topic><topic>regioselectivity</topic><topic>Stereoselectivity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yuan, Weiming</creatorcontrib><creatorcontrib>Zhang, Xue</creatorcontrib><creatorcontrib>Yu, Yihua</creatorcontrib><creatorcontrib>Ma, Shengming</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yuan, Weiming</au><au>Zhang, Xue</au><au>Yu, Yihua</au><au>Ma, Shengming</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Amide-Controlled Highly Selective Catalytic Borylcupration of Allenes</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. Eur. J</addtitle><date>2013-05-27</date><risdate>2013</risdate><volume>19</volume><issue>22</issue><spage>7193</spage><epage>7202</epage><pages>7193-7202</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>A novel copper‐catalyzed, highly regio‐ and stereoselective borylcupration of substituted 2,3‐allenamides with bis(pinacolato)diboron producing Z‐β‐borylated β,γ‐unsaturated enoamides has been demonstrated. Due to the unique effect of the amide‐group, perfect regio‐ and stereoselectivity and good to excellent yields have been achieved, which were rationalized by a DFT study.
Perfect selection! A copper‐catalyzed, highly regio‐ and stereoselective borylcupration of 2,3‐allenamide with bis(pinacolato)diboron producing Z‐β‐borylated β,γ‐unsaturated amides has been developed (see scheme; L=large, S=small). Due to the unique effect of the amide group, perfect regio‐ and stereoselectivity and good to excellent yields have been achieved. The results have been rationalized by a DFT study.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>23559155</pmid><doi>10.1002/chem.201202835</doi><tpages>10</tpages></addata></record> |
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| subjects | allenes Amides Beta boron Catalysis Catalysts Chemistry copper regioselectivity Stereoselectivity |
| title | Amide-Controlled Highly Selective Catalytic Borylcupration of Allenes |
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