Aryl‐to‐Vinyl 1,4‐Nickel Migration/Reductive Cross‐Coupling Reaction for the Stereoselective Synthesis of Multisubstituted Olefins
The aryl‐to‐vinyl nickel 1,4‐migration (1,4‐Ni migration) reaction has been reported for the first time. The generated alkenyl Ni species undergo a reductive coupling reaction with unactivated brominated alkanes affording a series of trisubstituted olefins. This tandem reaction exhibits mild conditi...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2023-07, Vol.62 (28), p.e202304447-n/a |
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| creator | Wang, Cui‐Tian Liang, Peng‐Yu Li, Ming Wang, Bin Wang, Yu‐Zhao Li, Xue‐Song Wei, Wan‐Xu Gou, Xue‐Ya Ding, Ya‐Nan Zhang, Zhe Li, Yu‐Ke Liu, Xue‐Yuan Liang, Yong‐Min |
| description | The aryl‐to‐vinyl nickel 1,4‐migration (1,4‐Ni migration) reaction has been reported for the first time. The generated alkenyl Ni species undergo a reductive coupling reaction with unactivated brominated alkanes affording a series of trisubstituted olefins. This tandem reaction exhibits mild conditions, a broad substrate scope, high regioselectivity, and excellent Z/E stereoselectivity. A series of controlled experiments have shown that the critical 1,4‐Ni migration process is reversible. In addition, the alkenyl nickel intermediates obtained after migration are highly Z/E stereoselective and do not undergo Z/E isomerization. The obtained trace isomerization products are caused by the instability of the product.
The 1,4‐nickel migration process from aryl to alkenyl groups is now reported for the first time. The alkenyl nickel intermediates generated by this highly stereoselective migration process can be coupled with brominated alkanes to form multisubstituted olefins. The current method provides a new and efficient approach for the synthesis of Z/E olefins with high stereoselectivity. |
| doi_str_mv | 10.1002/anie.202304447 |
| format | Article |
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The 1,4‐nickel migration process from aryl to alkenyl groups is now reported for the first time. The alkenyl nickel intermediates generated by this highly stereoselective migration process can be coupled with brominated alkanes to form multisubstituted olefins. The current method provides a new and efficient approach for the synthesis of Z/E olefins with high stereoselectivity.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.202304447</identifier><identifier>PMID: 37145118</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>1,4-Nickel Migration ; Alkanes ; Alkenes ; Aromatic compounds ; Bromination ; Cascade chemical reactions ; Chemical reactions ; Chemical synthesis ; Cross coupling ; C−H Activation ; Intermediates ; Isomerization ; Multisubstituted Olefins ; Nickel ; Reductive Cross-Coupling ; Regioselectivity ; Stereoselectivity ; Substrates ; Z/E Stereoselective</subject><ispartof>Angewandte Chemie International Edition, 2023-07, Vol.62 (28), p.e202304447-n/a</ispartof><rights>2023 Wiley‐VCH GmbH</rights><rights>2023 Wiley-VCH GmbH.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3737-fa66dea52477ff323194d7fcac138d13a39a883f2a15bedf582f4c704ebd06a03</citedby><cites>FETCH-LOGICAL-c3737-fa66dea52477ff323194d7fcac138d13a39a883f2a15bedf582f4c704ebd06a03</cites><orcidid>0000-0002-6167-6536</orcidid></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.202304447$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.202304447$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/37145118$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wang, Cui‐Tian</creatorcontrib><creatorcontrib>Liang, Peng‐Yu</creatorcontrib><creatorcontrib>Li, Ming</creatorcontrib><creatorcontrib>Wang, Bin</creatorcontrib><creatorcontrib>Wang, Yu‐Zhao</creatorcontrib><creatorcontrib>Li, Xue‐Song</creatorcontrib><creatorcontrib>Wei, Wan‐Xu</creatorcontrib><creatorcontrib>Gou, Xue‐Ya</creatorcontrib><creatorcontrib>Ding, Ya‐Nan</creatorcontrib><creatorcontrib>Zhang, Zhe</creatorcontrib><creatorcontrib>Li, Yu‐Ke</creatorcontrib><creatorcontrib>Liu, Xue‐Yuan</creatorcontrib><creatorcontrib>Liang, Yong‐Min</creatorcontrib><title>Aryl‐to‐Vinyl 1,4‐Nickel Migration/Reductive Cross‐Coupling Reaction for the Stereoselective Synthesis of Multisubstituted Olefins</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>The aryl‐to‐vinyl nickel 1,4‐migration (1,4‐Ni migration) reaction has been reported for the first time. The generated alkenyl Ni species undergo a reductive coupling reaction with unactivated brominated alkanes affording a series of trisubstituted olefins. This tandem reaction exhibits mild conditions, a broad substrate scope, high regioselectivity, and excellent Z/E stereoselectivity. A series of controlled experiments have shown that the critical 1,4‐Ni migration process is reversible. In addition, the alkenyl nickel intermediates obtained after migration are highly Z/E stereoselective and do not undergo Z/E isomerization. The obtained trace isomerization products are caused by the instability of the product.
The 1,4‐nickel migration process from aryl to alkenyl groups is now reported for the first time. The alkenyl nickel intermediates generated by this highly stereoselective migration process can be coupled with brominated alkanes to form multisubstituted olefins. The current method provides a new and efficient approach for the synthesis of Z/E olefins with high stereoselectivity.</description><subject>1,4-Nickel Migration</subject><subject>Alkanes</subject><subject>Alkenes</subject><subject>Aromatic compounds</subject><subject>Bromination</subject><subject>Cascade chemical reactions</subject><subject>Chemical reactions</subject><subject>Chemical synthesis</subject><subject>Cross coupling</subject><subject>C−H Activation</subject><subject>Intermediates</subject><subject>Isomerization</subject><subject>Multisubstituted Olefins</subject><subject>Nickel</subject><subject>Reductive Cross-Coupling</subject><subject>Regioselectivity</subject><subject>Stereoselectivity</subject><subject>Substrates</subject><subject>Z/E Stereoselective</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNqF0T1vFDEQBmALEZEQaCmRJRoK9mJ7vGtfeToFiJQPKQHalW93HBx868P2grajpuI35pfEp0uCRENjj6xnRta8hLzibMYZE0dmcDgTTACTUqon5IDXglegFDwttQSolK75Pnme0k3xWrPmGdkHxWXNuT4gvxdx8re__uRQji9umDzl72Spz133DT09c9fRZBeGo0vsxy67H0iXMaRUyDKMG--Ga3qJptsaakOk-SvSq4wRQ0KPu46raSjPySUaLD0bfXZpXKXs8pixpxcerRvSC7JnjU_48v4-JJ_fH39afqxOLz6cLBenVQcKVGVN0_RoaiGVshYE8Lnsle1Mx0H3HAzMjdZgheH1Cntba2Flp5jEVc8aw-CQvN3N3cTwfcSU27VLHXpvBgxjaoXmbC4AoC70zT_0JoxxKL8rCkQjykJ5UbOd6raLiWjbTXRrE6eWs3abUrtNqX1MqTS8vh87rtbYP_KHWAqY78BP53H6z7h2cX5y_Hf4HQJrpG4</recordid><startdate>20230710</startdate><enddate>20230710</enddate><creator>Wang, Cui‐Tian</creator><creator>Liang, Peng‐Yu</creator><creator>Li, Ming</creator><creator>Wang, Bin</creator><creator>Wang, Yu‐Zhao</creator><creator>Li, Xue‐Song</creator><creator>Wei, Wan‐Xu</creator><creator>Gou, Xue‐Ya</creator><creator>Ding, Ya‐Nan</creator><creator>Zhang, Zhe</creator><creator>Li, Yu‐Ke</creator><creator>Liu, Xue‐Yuan</creator><creator>Liang, Yong‐Min</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-6167-6536</orcidid></search><sort><creationdate>20230710</creationdate><title>Aryl‐to‐Vinyl 1,4‐Nickel Migration/Reductive Cross‐Coupling Reaction for the Stereoselective Synthesis of Multisubstituted Olefins</title><author>Wang, Cui‐Tian ; Liang, Peng‐Yu ; Li, Ming ; Wang, Bin ; Wang, Yu‐Zhao ; Li, Xue‐Song ; Wei, Wan‐Xu ; Gou, Xue‐Ya ; Ding, Ya‐Nan ; Zhang, Zhe ; Li, Yu‐Ke ; Liu, Xue‐Yuan ; Liang, Yong‐Min</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3737-fa66dea52477ff323194d7fcac138d13a39a883f2a15bedf582f4c704ebd06a03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>1,4-Nickel Migration</topic><topic>Alkanes</topic><topic>Alkenes</topic><topic>Aromatic compounds</topic><topic>Bromination</topic><topic>Cascade chemical reactions</topic><topic>Chemical reactions</topic><topic>Chemical synthesis</topic><topic>Cross coupling</topic><topic>C−H Activation</topic><topic>Intermediates</topic><topic>Isomerization</topic><topic>Multisubstituted Olefins</topic><topic>Nickel</topic><topic>Reductive Cross-Coupling</topic><topic>Regioselectivity</topic><topic>Stereoselectivity</topic><topic>Substrates</topic><topic>Z/E Stereoselective</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Cui‐Tian</creatorcontrib><creatorcontrib>Liang, Peng‐Yu</creatorcontrib><creatorcontrib>Li, Ming</creatorcontrib><creatorcontrib>Wang, Bin</creatorcontrib><creatorcontrib>Wang, Yu‐Zhao</creatorcontrib><creatorcontrib>Li, Xue‐Song</creatorcontrib><creatorcontrib>Wei, Wan‐Xu</creatorcontrib><creatorcontrib>Gou, Xue‐Ya</creatorcontrib><creatorcontrib>Ding, Ya‐Nan</creatorcontrib><creatorcontrib>Zhang, Zhe</creatorcontrib><creatorcontrib>Li, Yu‐Ke</creatorcontrib><creatorcontrib>Liu, Xue‐Yuan</creatorcontrib><creatorcontrib>Liang, Yong‐Min</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Cui‐Tian</au><au>Liang, Peng‐Yu</au><au>Li, Ming</au><au>Wang, Bin</au><au>Wang, Yu‐Zhao</au><au>Li, Xue‐Song</au><au>Wei, Wan‐Xu</au><au>Gou, Xue‐Ya</au><au>Ding, Ya‐Nan</au><au>Zhang, Zhe</au><au>Li, Yu‐Ke</au><au>Liu, Xue‐Yuan</au><au>Liang, Yong‐Min</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Aryl‐to‐Vinyl 1,4‐Nickel Migration/Reductive Cross‐Coupling Reaction for the Stereoselective Synthesis of Multisubstituted Olefins</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2023-07-10</date><risdate>2023</risdate><volume>62</volume><issue>28</issue><spage>e202304447</spage><epage>n/a</epage><pages>e202304447-n/a</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>The aryl‐to‐vinyl nickel 1,4‐migration (1,4‐Ni migration) reaction has been reported for the first time. The generated alkenyl Ni species undergo a reductive coupling reaction with unactivated brominated alkanes affording a series of trisubstituted olefins. This tandem reaction exhibits mild conditions, a broad substrate scope, high regioselectivity, and excellent Z/E stereoselectivity. A series of controlled experiments have shown that the critical 1,4‐Ni migration process is reversible. In addition, the alkenyl nickel intermediates obtained after migration are highly Z/E stereoselective and do not undergo Z/E isomerization. The obtained trace isomerization products are caused by the instability of the product.
The 1,4‐nickel migration process from aryl to alkenyl groups is now reported for the first time. The alkenyl nickel intermediates generated by this highly stereoselective migration process can be coupled with brominated alkanes to form multisubstituted olefins. The current method provides a new and efficient approach for the synthesis of Z/E olefins with high stereoselectivity.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>37145118</pmid><doi>10.1002/anie.202304447</doi><tpages>7</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0002-6167-6536</orcidid></addata></record> |
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| subjects | 1,4-Nickel Migration Alkanes Alkenes Aromatic compounds Bromination Cascade chemical reactions Chemical reactions Chemical synthesis Cross coupling C−H Activation Intermediates Isomerization Multisubstituted Olefins Nickel Reductive Cross-Coupling Regioselectivity Stereoselectivity Substrates Z/E Stereoselective |
| title | Aryl‐to‐Vinyl 1,4‐Nickel Migration/Reductive Cross‐Coupling Reaction for the Stereoselective Synthesis of Multisubstituted Olefins |
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