Nickel-Catalyzed Heck-Type Alkenylation of Secondary and Tertiary [alpha]-Carbonyl Alkyl Bromides

Ni made it! A novel Heck-type reaction of secondary and tertiary [alpha]-carbonyl alkyl bromides, most likely involving a radical process, was achieved through the use of a nickel catalyst. Various substituted styrenes and 1,1-diaryl alkenes were utilized as substrates to easily construct [alpha]-al...

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Veröffentlicht in:	Angewandte Chemie International Edition 2012-04, Vol.51 (15), p.3638-3641
Hauptverfasser:	Liu, Chao, Tang, Shan, Liu, Dong, Yuan, Jiwen, Zheng, Liwei, Meng, Lingkui, Lei, Aiwen
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkenes Bromides Carbon Carbonyl compounds Catalysis Catalysts Nickel Radicals Styrenes
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creator	Liu, Chao Tang, Shan Liu, Dong Yuan, Jiwen Zheng, Liwei Meng, Lingkui Lei, Aiwen
description	Ni made it! A novel Heck-type reaction of secondary and tertiary [alpha]-carbonyl alkyl bromides, most likely involving a radical process, was achieved through the use of a nickel catalyst. Various substituted styrenes and 1,1-diaryl alkenes were utilized as substrates to easily construct [alpha]-alkenyl carbonyl compounds with tertiary or quaternary carbon centers. A catalytic cycle involving Ni super(I)/Ni super(II) is proposed based on our experimental results. EWG=electron-withdrawing group.
doi_str_mv	10.1002/anie.201108350
format	Article
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A novel Heck-type reaction of secondary and tertiary [alpha]-carbonyl alkyl bromides, most likely involving a radical process, was achieved through the use of a nickel catalyst. Various substituted styrenes and 1,1-diaryl alkenes were utilized as substrates to easily construct [alpha]-alkenyl carbonyl compounds with tertiary or quaternary carbon centers. A catalytic cycle involving Ni super(I)/Ni super(II) is proposed based on our experimental results. 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EWG=electron-withdrawing group.</description><subject>Alkenes</subject><subject>Bromides</subject><subject>Carbon</subject><subject>Carbonyl compounds</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Nickel</subject><subject>Radicals</subject><subject>Styrenes</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNpdkL1PwzAQxS0EEqWwMkdiYXHxZ2yPpQKKhGCgTAhVdnwRad04xOkQ_npcwcRy9570u6enQ-iSkhklhN3YtoEZI5QSzSU5QhMqGcVcKX6cteAcKy3pKTpLaZN5rUk5Qfa5qbYQ8MIONozf4IslVFu8Gjso5mEL7Rjs0MS2iHXxClVsve3Hwra-WEE_NAfzbkP3aT9yRO9i5g93ed72cdd4SOfopLYhwcXfnqK3-7vVYomfXh4eF_Mn3FFRDtgrIksNXjhWARBhODglGBfAnWBAamedYUaCB0ad045X3OnaUuKFIcTzKbr-ze36-LWHNKx3TaogBNtC3Kc1VYfXGENURq_-oZu479vcbk0lLUsttRH8B05uZbU</recordid><startdate>20120410</startdate><enddate>20120410</enddate><creator>Liu, Chao</creator><creator>Tang, Shan</creator><creator>Liu, Dong</creator><creator>Yuan, Jiwen</creator><creator>Zheng, Liwei</creator><creator>Meng, Lingkui</creator><creator>Lei, Aiwen</creator><general>Wiley Subscription Services, Inc</general><scope>7TM</scope><scope>K9.</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20120410</creationdate><title>Nickel-Catalyzed Heck-Type Alkenylation of Secondary and Tertiary [alpha]-Carbonyl Alkyl Bromides</title><author>Liu, Chao ; Tang, Shan ; Liu, Dong ; Yuan, Jiwen ; Zheng, Liwei ; Meng, Lingkui ; Lei, Aiwen</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p146t-d70568ed4b2cee0493eb74234e3b42e0fbab9295ede21bb8b3c3b8fa10d4900d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Alkenes</topic><topic>Bromides</topic><topic>Carbon</topic><topic>Carbonyl compounds</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Nickel</topic><topic>Radicals</topic><topic>Styrenes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Chao</creatorcontrib><creatorcontrib>Tang, Shan</creatorcontrib><creatorcontrib>Liu, Dong</creatorcontrib><creatorcontrib>Yuan, Jiwen</creatorcontrib><creatorcontrib>Zheng, Liwei</creatorcontrib><creatorcontrib>Meng, Lingkui</creatorcontrib><creatorcontrib>Lei, Aiwen</creatorcontrib><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Chao</au><au>Tang, Shan</au><au>Liu, Dong</au><au>Yuan, Jiwen</au><au>Zheng, Liwei</au><au>Meng, Lingkui</au><au>Lei, Aiwen</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Nickel-Catalyzed Heck-Type Alkenylation of Secondary and Tertiary [alpha]-Carbonyl Alkyl Bromides</atitle><jtitle>Angewandte Chemie International Edition</jtitle><date>2012-04-10</date><risdate>2012</risdate><volume>51</volume><issue>15</issue><spage>3638</spage><epage>3641</epage><pages>3638-3641</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>Ni made it! A novel Heck-type reaction of secondary and tertiary [alpha]-carbonyl alkyl bromides, most likely involving a radical process, was achieved through the use of a nickel catalyst. Various substituted styrenes and 1,1-diaryl alkenes were utilized as substrates to easily construct [alpha]-alkenyl carbonyl compounds with tertiary or quaternary carbon centers. A catalytic cycle involving Ni super(I)/Ni super(II) is proposed based on our experimental results. EWG=electron-withdrawing group.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/anie.201108350</doi><tpages>4</tpages><edition>International ed. in English</edition></addata></record>
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source	Wiley Online Library Journals Frontfile Complete
subjects	Alkenes Bromides Carbon Carbonyl compounds Catalysis Catalysts Nickel Radicals Styrenes
title	Nickel-Catalyzed Heck-Type Alkenylation of Secondary and Tertiary [alpha]-Carbonyl Alkyl Bromides
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