Co/Zn Bimetallic Catalysis Enables Enantioselective Alkynylation of Isatins and α‑Ketoesters Using Terminal Alkynes

We present herein a novel cobalt/zinc bimetallic catalysis system for the realization of an efficient and enantioselective alkynylation of isatins and α-ketoesters using terminal alkynes. By using a simple procedure with all commercially available catalysts, including cobalt bromide, a chiral bispho...

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Veröffentlicht in:	Journal of organic chemistry 2023-06, Vol.88 (12), p.7755-7763
Hauptverfasser:	Huang, Rui-Zhi, Ma, Zhan-Cai, Huang, Yuan, Zhao, Yu
Format:	Artikel
Sprache:	eng
Schlagworte:	Alcohols Alkynes Catalysis Cobalt Isatin Stereoisomerism Zinc
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container_end_page	7763
container_issue	12
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container_title	Journal of organic chemistry
container_volume	88
creator	Huang, Rui-Zhi Ma, Zhan-Cai Huang, Yuan Zhao, Yu
description	We present herein a novel cobalt/zinc bimetallic catalysis system for the realization of an efficient and enantioselective alkynylation of isatins and α-ketoesters using terminal alkynes. By using a simple procedure with all commercially available catalysts, including cobalt bromide, a chiral bisphosphine ligand, and zinc triflate, a range of synthetically useful tertiary propargylic alcohols are accessed with high yields and good enantioselectivities. Control reactions showed that this catalytic system proceeds through activation of the terminal alkyne by zinc triflate and a base, transmetalation from zinc to cobalt, and then the enantio-determining alkynylation of ketones.
doi_str_mv	10.1021/acs.joc.2c01369
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By using a simple procedure with all commercially available catalysts, including cobalt bromide, a chiral bisphosphine ligand, and zinc triflate, a range of synthetically useful tertiary propargylic alcohols are accessed with high yields and good enantioselectivities. Control reactions showed that this catalytic system proceeds through activation of the terminal alkyne by zinc triflate and a base, transmetalation from zinc to cobalt, and then the enantio-determining alkynylation of ketones.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.2c01369</identifier><identifier>PMID: 36314376</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Alcohols ; Alkynes ; Catalysis ; Cobalt ; Isatin ; Stereoisomerism ; Zinc</subject><ispartof>Journal of organic chemistry, 2023-06, Vol.88 (12), p.7755-7763</ispartof><rights>2022 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a333t-8792372a784ada676e682511d5958306f0e069604a0c67bcf1497b3383cdad213</citedby><cites>FETCH-LOGICAL-a333t-8792372a784ada676e682511d5958306f0e069604a0c67bcf1497b3383cdad213</cites><orcidid>0000-0002-2944-1315</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.joc.2c01369$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.joc.2c01369$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,777,781,2752,27057,27905,27906,56719,56769</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36314376$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Huang, Rui-Zhi</creatorcontrib><creatorcontrib>Ma, Zhan-Cai</creatorcontrib><creatorcontrib>Huang, Yuan</creatorcontrib><creatorcontrib>Zhao, Yu</creatorcontrib><title>Co/Zn Bimetallic Catalysis Enables Enantioselective Alkynylation of Isatins and α‑Ketoesters Using Terminal Alkynes</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>We present herein a novel cobalt/zinc bimetallic catalysis system for the realization of an efficient and enantioselective alkynylation of isatins and α-ketoesters using terminal alkynes. By using a simple procedure with all commercially available catalysts, including cobalt bromide, a chiral bisphosphine ligand, and zinc triflate, a range of synthetically useful tertiary propargylic alcohols are accessed with high yields and good enantioselectivities. Control reactions showed that this catalytic system proceeds through activation of the terminal alkyne by zinc triflate and a base, transmetalation from zinc to cobalt, and then the enantio-determining alkynylation of ketones.</description><subject>Alcohols</subject><subject>Alkynes</subject><subject>Catalysis</subject><subject>Cobalt</subject><subject>Isatin</subject><subject>Stereoisomerism</subject><subject>Zinc</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNp1kDtOxDAQhi0EguVR0yGXSCi7fiR2UsKKl0CigYYm8joTZHAcyGRX2o4rcBQuwiE4CYYsdLiZkfX9v0YfIfucjTkTfGIsjh9bOxaWcamKNTLimWCJKli6TkaMCZFIoeQW2UZ8ZPFlWbZJtqSSPJVajchi2k7uAz1xDfTGe2fp1MRliQ7paTAzDz8z9K5F8GB7twB67J-WYelN_Ay0reklxjUgNaGiH--fr29X0LeAPXRI79CFB3oLXeOC8UMUcJds1MYj7K3mDrk7O72dXiTXN-eX0-PrxEgp-yTXhZBaGJ2npjJKK1C5yDivsiLLJVM1A6YKxVLDrNIzW_O00DMpc2krUwkud8jh0PvctS_zeFLZOLTgvQnQzrEUOrakOlUqopMBtV2L2EFdPneuMd2y5Kz8ll1G2WWUXa5kx8TBqnw-a6D643_tRuBoAIbkvIsG8N-6L9sMjEw</recordid><startdate>20230616</startdate><enddate>20230616</enddate><creator>Huang, Rui-Zhi</creator><creator>Ma, Zhan-Cai</creator><creator>Huang, Yuan</creator><creator>Zhao, Yu</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-2944-1315</orcidid></search><sort><creationdate>20230616</creationdate><title>Co/Zn Bimetallic Catalysis Enables Enantioselective Alkynylation of Isatins and α‑Ketoesters Using Terminal Alkynes</title><author>Huang, Rui-Zhi ; Ma, Zhan-Cai ; Huang, Yuan ; Zhao, Yu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a333t-8792372a784ada676e682511d5958306f0e069604a0c67bcf1497b3383cdad213</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Alcohols</topic><topic>Alkynes</topic><topic>Catalysis</topic><topic>Cobalt</topic><topic>Isatin</topic><topic>Stereoisomerism</topic><topic>Zinc</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Huang, Rui-Zhi</creatorcontrib><creatorcontrib>Ma, Zhan-Cai</creatorcontrib><creatorcontrib>Huang, Yuan</creatorcontrib><creatorcontrib>Zhao, Yu</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Huang, Rui-Zhi</au><au>Ma, Zhan-Cai</au><au>Huang, Yuan</au><au>Zhao, Yu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Co/Zn Bimetallic Catalysis Enables Enantioselective Alkynylation of Isatins and α‑Ketoesters Using Terminal Alkynes</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2023-06-16</date><risdate>2023</risdate><volume>88</volume><issue>12</issue><spage>7755</spage><epage>7763</epage><pages>7755-7763</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>We present herein a novel cobalt/zinc bimetallic catalysis system for the realization of an efficient and enantioselective alkynylation of isatins and α-ketoesters using terminal alkynes. By using a simple procedure with all commercially available catalysts, including cobalt bromide, a chiral bisphosphine ligand, and zinc triflate, a range of synthetically useful tertiary propargylic alcohols are accessed with high yields and good enantioselectivities. Control reactions showed that this catalytic system proceeds through activation of the terminal alkyne by zinc triflate and a base, transmetalation from zinc to cobalt, and then the enantio-determining alkynylation of ketones.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>36314376</pmid><doi>10.1021/acs.joc.2c01369</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0002-2944-1315</orcidid></addata></record>
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subjects	Alcohols Alkynes Catalysis Cobalt Isatin Stereoisomerism Zinc
title	Co/Zn Bimetallic Catalysis Enables Enantioselective Alkynylation of Isatins and α‑Ketoesters Using Terminal Alkynes
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