Radical‐Mediated 1,2‐Difunctionalization of Alkenes with Nucleophiles and Acetonitrile through C(sp3)−H Bond Cleavage

Radical‐Mediated 1,2‐Difunctionalization of Alkenes with Nucleophiles and Acetonitrile through C(sp3)−H Bond Cleavage

A cobalt‐catalyzed intermolecular 1,2‐difunctionalization of alkenes with anilines/indoles and acetonitrile has been developed. This protocol provides an access to functionalized cyano‐containing molecules. In this transformation, employing di‐tert‐butyl peroxide as a radical initiator, a variety of...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Advanced synthesis & catalysis 2024-01, Vol.366 (1), p.56-61
Hauptverfasser: Zhu, Fengxiang, Yang, Yifan, Shi, Shanshan
Format: Artikel
Sprache:eng
Schlagworte:
1,2-Difunctionalization
Acetonitrile
Alkene
Alkenes
Aniline
Aromatic compounds
C(sp3)−H bond cleavage
Cobalt
Commercialization
Indoles
Isotope effect
Multicomponent reaction
Nucleophiles
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 61
container_issue 1
container_start_page 56
container_title Advanced synthesis & catalysis
container_volume 366
creator Zhu, Fengxiang
Yang, Yifan
Shi, Shanshan
description A cobalt‐catalyzed intermolecular 1,2‐difunctionalization of alkenes with anilines/indoles and acetonitrile has been developed. This protocol provides an access to functionalized cyano‐containing molecules. In this transformation, employing di‐tert‐butyl peroxide as a radical initiator, a variety of commercialized nucleophiles and electronically diverse arenes were well tolerated. In addition, we also studied the kinetic isotope effect.
doi_str_mv 10.1002/adsc.202300956
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2912905637</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2912905637</sourcerecordid><originalsourceid>FETCH-LOGICAL-c2726-616cff16dd8f53a0a7c7bf68ea954e41570a35ec70aef6ac8f4fce7a89c66cee3</originalsourceid><addsrcrecordid>eNqFUD1PwzAUjBBIlMLKbIkFJFLspLGTsaRAkQpIfMzRw3luXUJc4oSqsDAyIn5ifwmuisrIdPdOd0-687x9RjuM0uAEcis7AQ1CSpOIb3gtxlnkdxlPNtc8otvejrUTSpmIhWh577eQawnF4uPrCnMNNeaEHQfu7GvVlLLWpoRCv8GSEKNIr3jCEi2Z6XpMrhtZoJmOdeEUKHPSk1ibUteVU0g9rkwzGpP00E7Do8Xn94CcGmdKC4RXGOGut6WgsLj3i23v4fzsPh34w5uLy7Q39GUgAu5zxqVSjOd5rKIQKAgpHhWPEZKoi66ToBBGKB2g4iBj1VUSBcSJ5Fwihm3vYPV3WpmXBm2dTUxTuVo2CxIWJDTioXCuzsolK2NthSqbVvoZqnnGaLYcOFsOnK0HdoFkFZi5svN_3Fmvf5f-ZX8AswCDyg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2912905637</pqid></control><display><type>article</type><title>Radical‐Mediated 1,2‐Difunctionalization of Alkenes with Nucleophiles and Acetonitrile through C(sp3)−H Bond Cleavage</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Zhu, Fengxiang ; Yang, Yifan ; Shi, Shanshan</creator><creatorcontrib>Zhu, Fengxiang ; Yang, Yifan ; Shi, Shanshan</creatorcontrib><description>A cobalt‐catalyzed intermolecular 1,2‐difunctionalization of alkenes with anilines/indoles and acetonitrile has been developed. This protocol provides an access to functionalized cyano‐containing molecules. In this transformation, employing di‐tert‐butyl peroxide as a radical initiator, a variety of commercialized nucleophiles and electronically diverse arenes were well tolerated. In addition, we also studied the kinetic isotope effect.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.202300956</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>1,2-Difunctionalization ; Acetonitrile ; Alkene ; Alkenes ; Aniline ; Aromatic compounds ; C(sp3)−H bond cleavage ; Cobalt ; Commercialization ; Indoles ; Isotope effect ; Multicomponent reaction ; Nucleophiles</subject><ispartof>Advanced synthesis &amp; catalysis, 2024-01, Vol.366 (1), p.56-61</ispartof><rights>2023 Wiley‐VCH GmbH</rights><rights>2024 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c2726-616cff16dd8f53a0a7c7bf68ea954e41570a35ec70aef6ac8f4fce7a89c66cee3</cites><orcidid>0000-0001-9551-4618</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%2Fadsc.202300956$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fadsc.202300956$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Zhu, Fengxiang</creatorcontrib><creatorcontrib>Yang, Yifan</creatorcontrib><creatorcontrib>Shi, Shanshan</creatorcontrib><title>Radical‐Mediated 1,2‐Difunctionalization of Alkenes with Nucleophiles and Acetonitrile through C(sp3)−H Bond Cleavage</title><title>Advanced synthesis &amp; catalysis</title><description>A cobalt‐catalyzed intermolecular 1,2‐difunctionalization of alkenes with anilines/indoles and acetonitrile has been developed. This protocol provides an access to functionalized cyano‐containing molecules. In this transformation, employing di‐tert‐butyl peroxide as a radical initiator, a variety of commercialized nucleophiles and electronically diverse arenes were well tolerated. In addition, we also studied the kinetic isotope effect.</description><subject>1,2-Difunctionalization</subject><subject>Acetonitrile</subject><subject>Alkene</subject><subject>Alkenes</subject><subject>Aniline</subject><subject>Aromatic compounds</subject><subject>C(sp3)−H bond cleavage</subject><subject>Cobalt</subject><subject>Commercialization</subject><subject>Indoles</subject><subject>Isotope effect</subject><subject>Multicomponent reaction</subject><subject>Nucleophiles</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNqFUD1PwzAUjBBIlMLKbIkFJFLspLGTsaRAkQpIfMzRw3luXUJc4oSqsDAyIn5ifwmuisrIdPdOd0-687x9RjuM0uAEcis7AQ1CSpOIb3gtxlnkdxlPNtc8otvejrUTSpmIhWh577eQawnF4uPrCnMNNeaEHQfu7GvVlLLWpoRCv8GSEKNIr3jCEi2Z6XpMrhtZoJmOdeEUKHPSk1ibUteVU0g9rkwzGpP00E7Do8Xn94CcGmdKC4RXGOGut6WgsLj3i23v4fzsPh34w5uLy7Q39GUgAu5zxqVSjOd5rKIQKAgpHhWPEZKoi66ToBBGKB2g4iBj1VUSBcSJ5Fwihm3vYPV3WpmXBm2dTUxTuVo2CxIWJDTioXCuzsolK2NthSqbVvoZqnnGaLYcOFsOnK0HdoFkFZi5svN_3Fmvf5f-ZX8AswCDyg</recordid><startdate>20240109</startdate><enddate>20240109</enddate><creator>Zhu, Fengxiang</creator><creator>Yang, Yifan</creator><creator>Shi, Shanshan</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0001-9551-4618</orcidid></search><sort><creationdate>20240109</creationdate><title>Radical‐Mediated 1,2‐Difunctionalization of Alkenes with Nucleophiles and Acetonitrile through C(sp3)−H Bond Cleavage</title><author>Zhu, Fengxiang ; Yang, Yifan ; Shi, Shanshan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2726-616cff16dd8f53a0a7c7bf68ea954e41570a35ec70aef6ac8f4fce7a89c66cee3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>1,2-Difunctionalization</topic><topic>Acetonitrile</topic><topic>Alkene</topic><topic>Alkenes</topic><topic>Aniline</topic><topic>Aromatic compounds</topic><topic>C(sp3)−H bond cleavage</topic><topic>Cobalt</topic><topic>Commercialization</topic><topic>Indoles</topic><topic>Isotope effect</topic><topic>Multicomponent reaction</topic><topic>Nucleophiles</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhu, Fengxiang</creatorcontrib><creatorcontrib>Yang, Yifan</creatorcontrib><creatorcontrib>Shi, Shanshan</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis &amp; catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhu, Fengxiang</au><au>Yang, Yifan</au><au>Shi, Shanshan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Radical‐Mediated 1,2‐Difunctionalization of Alkenes with Nucleophiles and Acetonitrile through C(sp3)−H Bond Cleavage</atitle><jtitle>Advanced synthesis &amp; catalysis</jtitle><date>2024-01-09</date><risdate>2024</risdate><volume>366</volume><issue>1</issue><spage>56</spage><epage>61</epage><pages>56-61</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>A cobalt‐catalyzed intermolecular 1,2‐difunctionalization of alkenes with anilines/indoles and acetonitrile has been developed. This protocol provides an access to functionalized cyano‐containing molecules. In this transformation, employing di‐tert‐butyl peroxide as a radical initiator, a variety of commercialized nucleophiles and electronically diverse arenes were well tolerated. In addition, we also studied the kinetic isotope effect.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.202300956</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0001-9551-4618</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1615-4150
ispartof Advanced synthesis & catalysis, 2024-01, Vol.366 (1), p.56-61
issn 1615-4150
1615-4169
language eng
recordid cdi_proquest_journals_2912905637
source Wiley Online Library Journals Frontfile Complete
subjects 1,2-Difunctionalization
Acetonitrile
Alkene
Alkenes
Aniline
Aromatic compounds
C(sp3)−H bond cleavage
Cobalt
Commercialization
Indoles
Isotope effect
Multicomponent reaction
Nucleophiles
title Radical‐Mediated 1,2‐Difunctionalization of Alkenes with Nucleophiles and Acetonitrile through C(sp3)−H Bond Cleavage
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-03T03%3A13%3A54IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Radical%E2%80%90Mediated%201,2%E2%80%90Difunctionalization%20of%20Alkenes%20with%20Nucleophiles%20and%20Acetonitrile%20through%20C(sp3)%E2%88%92H%20Bond%20Cleavage&rft.jtitle=Advanced%20synthesis%20&%20catalysis&rft.au=Zhu,%20Fengxiang&rft.date=2024-01-09&rft.volume=366&rft.issue=1&rft.spage=56&rft.epage=61&rft.pages=56-61&rft.issn=1615-4150&rft.eissn=1615-4169&rft_id=info:doi/10.1002/adsc.202300956&rft_dat=%3Cproquest_cross%3E2912905637%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2912905637&rft_id=info:pmid/&rfr_iscdi=true