Divergent Aminocarbonylations of Alkynes Enabled by Photoredox/Nickel Dual Catalysis
A metallaphotoredox‐catalyzed strategy for the selective and divergent aminocarbonylation of alkynes with amines and 1 atm of CO is reported. This synergistic protocol not only enables the Markovnikov‐selective hydroaminocarbonylation of alkynes to afford α,β‐unsaturated amides, but also facilitates...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2021-12, Vol.60 (51), p.26511-26517 |
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| creator | Zhao, Xian Feng, Xiaoliang Chen, Fan Zhu, Shengqing Qing, Feng‐Ling Chu, Lingling |
| description | A metallaphotoredox‐catalyzed strategy for the selective and divergent aminocarbonylation of alkynes with amines and 1 atm of CO is reported. This synergistic protocol not only enables the Markovnikov‐selective hydroaminocarbonylation of alkynes to afford α,β‐unsaturated amides, but also facilitates a sequential four‐component hydroaminocarbonylation/radical alkylation in the presence of tertiary and secondary alkyl boronate esters, which allows for straightforward conversion of alkynes into corresponding amides. Preliminary mechanistic studies disclose that a photoinduced oxidative insertion of aniline and CO into nickel followed by a migratory insertion of (carbamoyl)nickel species could be involved.
A metallaphotoredox‐catalyzed strategy for the Markovnikov‐selective hydroaminocarbonylation of alkynes with amines and 1 atm of CO is reported, offering a novel and complementary platform for accessing α,β‐unsaturated amides. This synergistic protocol facilitates an unprecedented sequential hydroaminocarbonylation/radical alkylation process with tertiary and secondary alkyl boronate esters. |
| doi_str_mv | 10.1002/anie.202111061 |
| format | Article |
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A metallaphotoredox‐catalyzed strategy for the Markovnikov‐selective hydroaminocarbonylation of alkynes with amines and 1 atm of CO is reported, offering a novel and complementary platform for accessing α,β‐unsaturated amides. This synergistic protocol facilitates an unprecedented sequential hydroaminocarbonylation/radical alkylation process with tertiary and secondary alkyl boronate esters.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.202111061</identifier><identifier>PMID: 34651398</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Alkylation ; Alkynes ; Amides ; Amines ; Aniline ; Carbon monoxide ; Catalysis ; Divergence ; divergent ; Esters ; hydroaminocarbonylation ; Insertion ; Nickel ; nickel catalysis ; photoredox catalysis ; sequential catalysis</subject><ispartof>Angewandte Chemie International Edition, 2021-12, Vol.60 (51), p.26511-26517</ispartof><rights>2021 Wiley‐VCH GmbH</rights><rights>2021 Wiley-VCH GmbH.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3731-fd14a28e9827c8b6cfc7446a72d625af561458489c84331a87a729987dc06a0f3</citedby><cites>FETCH-LOGICAL-c3731-fd14a28e9827c8b6cfc7446a72d625af561458489c84331a87a729987dc06a0f3</cites><orcidid>0000-0001-7969-0531</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.202111061$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.202111061$$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/34651398$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhao, Xian</creatorcontrib><creatorcontrib>Feng, Xiaoliang</creatorcontrib><creatorcontrib>Chen, Fan</creatorcontrib><creatorcontrib>Zhu, Shengqing</creatorcontrib><creatorcontrib>Qing, Feng‐Ling</creatorcontrib><creatorcontrib>Chu, Lingling</creatorcontrib><title>Divergent Aminocarbonylations of Alkynes Enabled by Photoredox/Nickel Dual Catalysis</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>A metallaphotoredox‐catalyzed strategy for the selective and divergent aminocarbonylation of alkynes with amines and 1 atm of CO is reported. This synergistic protocol not only enables the Markovnikov‐selective hydroaminocarbonylation of alkynes to afford α,β‐unsaturated amides, but also facilitates a sequential four‐component hydroaminocarbonylation/radical alkylation in the presence of tertiary and secondary alkyl boronate esters, which allows for straightforward conversion of alkynes into corresponding amides. Preliminary mechanistic studies disclose that a photoinduced oxidative insertion of aniline and CO into nickel followed by a migratory insertion of (carbamoyl)nickel species could be involved.
A metallaphotoredox‐catalyzed strategy for the Markovnikov‐selective hydroaminocarbonylation of alkynes with amines and 1 atm of CO is reported, offering a novel and complementary platform for accessing α,β‐unsaturated amides. This synergistic protocol facilitates an unprecedented sequential hydroaminocarbonylation/radical alkylation process with tertiary and secondary alkyl boronate esters.</description><subject>Alkylation</subject><subject>Alkynes</subject><subject>Amides</subject><subject>Amines</subject><subject>Aniline</subject><subject>Carbon monoxide</subject><subject>Catalysis</subject><subject>Divergence</subject><subject>divergent</subject><subject>Esters</subject><subject>hydroaminocarbonylation</subject><subject>Insertion</subject><subject>Nickel</subject><subject>nickel catalysis</subject><subject>photoredox catalysis</subject><subject>sequential catalysis</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqFkLtPwzAQhy0EorxWRhSJhSWtH4ntjFVboBICBpgtx3HA4NpgJ0D-e1yVh8TCdCfddz_dfQAcIzhGEOKJdEaPMcQIIUjRFthDJUY5YYxsp74gJGe8RCOwH-NT4jmHdBeMSEFLRCq-B-7m5k2HB-26bLoyzisZau8GKzvjXcx8m03t8-B0zBZO1lY3WT1kt4--80E3_mNybdSzttm8lzabyU7aIZp4CHZaaaM--qoH4P58cTe7zK9uLpaz6VWuCCMobxtUSMx1xTFTvKaqVawoqGS4obiUbUlRUfKCV4qnR5DkLI2qirNGQSphSw7A2Sb3JfjXXsdOrExU2lrptO-jwCXHHHJclAk9_YM--T64dJ3AFNIK8QrjRI03lAo-xqBb8RLMSoZBICjWvsXat_jxnRZOvmL7eqWbH_xbcAKqDfBurB7-iRPT6-XiN_wTvkaK-Q</recordid><startdate>20211213</startdate><enddate>20211213</enddate><creator>Zhao, Xian</creator><creator>Feng, Xiaoliang</creator><creator>Chen, Fan</creator><creator>Zhu, Shengqing</creator><creator>Qing, Feng‐Ling</creator><creator>Chu, Lingling</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/0000-0001-7969-0531</orcidid></search><sort><creationdate>20211213</creationdate><title>Divergent Aminocarbonylations of Alkynes Enabled by Photoredox/Nickel Dual Catalysis</title><author>Zhao, Xian ; Feng, Xiaoliang ; Chen, Fan ; Zhu, Shengqing ; Qing, Feng‐Ling ; Chu, Lingling</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3731-fd14a28e9827c8b6cfc7446a72d625af561458489c84331a87a729987dc06a0f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Alkylation</topic><topic>Alkynes</topic><topic>Amides</topic><topic>Amines</topic><topic>Aniline</topic><topic>Carbon monoxide</topic><topic>Catalysis</topic><topic>Divergence</topic><topic>divergent</topic><topic>Esters</topic><topic>hydroaminocarbonylation</topic><topic>Insertion</topic><topic>Nickel</topic><topic>nickel catalysis</topic><topic>photoredox catalysis</topic><topic>sequential catalysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhao, Xian</creatorcontrib><creatorcontrib>Feng, Xiaoliang</creatorcontrib><creatorcontrib>Chen, Fan</creatorcontrib><creatorcontrib>Zhu, Shengqing</creatorcontrib><creatorcontrib>Qing, Feng‐Ling</creatorcontrib><creatorcontrib>Chu, Lingling</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>Zhao, Xian</au><au>Feng, Xiaoliang</au><au>Chen, Fan</au><au>Zhu, Shengqing</au><au>Qing, Feng‐Ling</au><au>Chu, Lingling</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Divergent Aminocarbonylations of Alkynes Enabled by Photoredox/Nickel Dual Catalysis</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2021-12-13</date><risdate>2021</risdate><volume>60</volume><issue>51</issue><spage>26511</spage><epage>26517</epage><pages>26511-26517</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>A metallaphotoredox‐catalyzed strategy for the selective and divergent aminocarbonylation of alkynes with amines and 1 atm of CO is reported. This synergistic protocol not only enables the Markovnikov‐selective hydroaminocarbonylation of alkynes to afford α,β‐unsaturated amides, but also facilitates a sequential four‐component hydroaminocarbonylation/radical alkylation in the presence of tertiary and secondary alkyl boronate esters, which allows for straightforward conversion of alkynes into corresponding amides. Preliminary mechanistic studies disclose that a photoinduced oxidative insertion of aniline and CO into nickel followed by a migratory insertion of (carbamoyl)nickel species could be involved.
A metallaphotoredox‐catalyzed strategy for the Markovnikov‐selective hydroaminocarbonylation of alkynes with amines and 1 atm of CO is reported, offering a novel and complementary platform for accessing α,β‐unsaturated amides. This synergistic protocol facilitates an unprecedented sequential hydroaminocarbonylation/radical alkylation process with tertiary and secondary alkyl boronate esters.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>34651398</pmid><doi>10.1002/anie.202111061</doi><tpages>7</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0001-7969-0531</orcidid></addata></record> |
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| subjects | Alkylation Alkynes Amides Amines Aniline Carbon monoxide Catalysis Divergence divergent Esters hydroaminocarbonylation Insertion Nickel nickel catalysis photoredox catalysis sequential catalysis |
| title | Divergent Aminocarbonylations of Alkynes Enabled by Photoredox/Nickel Dual Catalysis |
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