Synthesis of P-stereogenic cyclicphosphinic amides via electrochemically enabled cobalt-catalyzed enantioselective C–H annulation
The development of an electrochemical process method for the synthesis of P-chiral phosphine derivatives poses a considerable challenge. Here, we present an electricity-driven cobalt-catalyzed enantioselective C–H annulation of arylphosphinic amides and alkynes, which provides rapid access to P-chir...
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Veröffentlicht in: | Green chemistry : an international journal and green chemistry resource : GC 2023-05, Vol.25 (9), p.3606-3614 |
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creator | Liu, Tao Zhang, Wangqin Xu, Chao Xu, Zhenhui Song, Dingguo Qian, Wei Lu, Gang Zhang, Chang-Jun Zhong, Weihui Ling, Fei |
description | The development of an electrochemical process method for the synthesis of P-chiral phosphine derivatives poses a considerable challenge. Here, we present an electricity-driven cobalt-catalyzed enantioselective C–H annulation of arylphosphinic amides and alkynes, which provides rapid access to P-chiral cyclicphosphorus oxides in good yields with excellent enantioselectivities (48–99% yields, 94–>99% ee). The reaction was compatible with aqueous solvents and proceeded efficiently in a shorter reaction time compared with the previous work using oxidants. The process employs a combination of readily available chiral salicyloxazoline and cobalt acetate tetrahydrate as an inexpensive catalyst. Notably, the kinetic resolution process was also achieved with
s
factors up to 347.8. Experimental, kinetic and computational studies on cobalta-electrocatalysis provide insights into the catalyst's working mode. |
doi_str_mv | 10.1039/D3GC00455D |
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s
factors up to 347.8. Experimental, kinetic and computational studies on cobalta-electrocatalysis provide insights into the catalyst's working mode.</description><identifier>ISSN: 1463-9262</identifier><identifier>EISSN: 1463-9270</identifier><identifier>DOI: 10.1039/D3GC00455D</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Acetic acid ; Alkynes ; Amides ; Catalysts ; Chemical reactions ; Chemical synthesis ; Cobalt ; Cobalt acetates ; Electrochemistry ; Enantiomers ; Green chemistry ; Organic chemistry ; Oxidants ; Oxidizing agents ; Phosphine ; Phosphines</subject><ispartof>Green chemistry : an international journal and green chemistry resource : GC, 2023-05, Vol.25 (9), p.3606-3614</ispartof><rights>Copyright Royal Society of Chemistry 2023</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c259t-af166cdf82cb269838b64a83f72c9c22be03138f4e512e7094e4cea2a1d152c3</citedby><cites>FETCH-LOGICAL-c259t-af166cdf82cb269838b64a83f72c9c22be03138f4e512e7094e4cea2a1d152c3</cites><orcidid>0000-0002-4274-912X ; 0000-0003-0349-2226</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27922,27923</link.rule.ids></links><search><creatorcontrib>Liu, Tao</creatorcontrib><creatorcontrib>Zhang, Wangqin</creatorcontrib><creatorcontrib>Xu, Chao</creatorcontrib><creatorcontrib>Xu, Zhenhui</creatorcontrib><creatorcontrib>Song, Dingguo</creatorcontrib><creatorcontrib>Qian, Wei</creatorcontrib><creatorcontrib>Lu, Gang</creatorcontrib><creatorcontrib>Zhang, Chang-Jun</creatorcontrib><creatorcontrib>Zhong, Weihui</creatorcontrib><creatorcontrib>Ling, Fei</creatorcontrib><title>Synthesis of P-stereogenic cyclicphosphinic amides via electrochemically enabled cobalt-catalyzed enantioselective C–H annulation</title><title>Green chemistry : an international journal and green chemistry resource : GC</title><description>The development of an electrochemical process method for the synthesis of P-chiral phosphine derivatives poses a considerable challenge. Here, we present an electricity-driven cobalt-catalyzed enantioselective C–H annulation of arylphosphinic amides and alkynes, which provides rapid access to P-chiral cyclicphosphorus oxides in good yields with excellent enantioselectivities (48–99% yields, 94–>99% ee). The reaction was compatible with aqueous solvents and proceeded efficiently in a shorter reaction time compared with the previous work using oxidants. The process employs a combination of readily available chiral salicyloxazoline and cobalt acetate tetrahydrate as an inexpensive catalyst. Notably, the kinetic resolution process was also achieved with
s
factors up to 347.8. Experimental, kinetic and computational studies on cobalta-electrocatalysis provide insights into the catalyst's working mode.</description><subject>Acetic acid</subject><subject>Alkynes</subject><subject>Amides</subject><subject>Catalysts</subject><subject>Chemical reactions</subject><subject>Chemical synthesis</subject><subject>Cobalt</subject><subject>Cobalt acetates</subject><subject>Electrochemistry</subject><subject>Enantiomers</subject><subject>Green chemistry</subject><subject>Organic chemistry</subject><subject>Oxidants</subject><subject>Oxidizing agents</subject><subject>Phosphine</subject><subject>Phosphines</subject><issn>1463-9262</issn><issn>1463-9270</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpFkN1Kw0AQhYMoWKs3PsGCd0J0f_J7Kam2gqBg78NmMjFbtrtxNy3EK8FH8A19ElMrejXDOWfmwBcE54xeMSry65mYF5RGcTw7CCYsSkSY85Qe_u0JPw5OvF9RyliaRJPg43kwfYteeWIb8hT6Hh3aFzQKCAygFXSt9V2rdoJcqxo92SpJUCP0zkKLawVS64GgkZXGmoCtpO5DkL3Uw9sojIbplfU_J2qLpPh6_1wQacxGy9Ewp8FRI7XHs985DZZ3t8tiET48zu-Lm4cQeJz3oWxYkkDdZBwqnuSZyKokkploUg45cF4hFUxkTYQx45jSPMIIUHLJahZzENPgYv-2c_Z1g74vV3bjzNhY8oyNPDjLxZi63KfAWe8dNmXn1Fq6oWS03DEu_xmLb3EccnI</recordid><startdate>20230509</startdate><enddate>20230509</enddate><creator>Liu, Tao</creator><creator>Zhang, Wangqin</creator><creator>Xu, Chao</creator><creator>Xu, Zhenhui</creator><creator>Song, Dingguo</creator><creator>Qian, Wei</creator><creator>Lu, Gang</creator><creator>Zhang, Chang-Jun</creator><creator>Zhong, Weihui</creator><creator>Ling, Fei</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7ST</scope><scope>7U6</scope><scope>8BQ</scope><scope>8FD</scope><scope>C1K</scope><scope>JG9</scope><orcidid>https://orcid.org/0000-0002-4274-912X</orcidid><orcidid>https://orcid.org/0000-0003-0349-2226</orcidid></search><sort><creationdate>20230509</creationdate><title>Synthesis of P-stereogenic cyclicphosphinic amides via electrochemically enabled cobalt-catalyzed enantioselective C–H annulation</title><author>Liu, Tao ; Zhang, Wangqin ; Xu, Chao ; Xu, Zhenhui ; Song, Dingguo ; Qian, Wei ; Lu, Gang ; Zhang, Chang-Jun ; Zhong, Weihui ; Ling, Fei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c259t-af166cdf82cb269838b64a83f72c9c22be03138f4e512e7094e4cea2a1d152c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Acetic acid</topic><topic>Alkynes</topic><topic>Amides</topic><topic>Catalysts</topic><topic>Chemical reactions</topic><topic>Chemical synthesis</topic><topic>Cobalt</topic><topic>Cobalt acetates</topic><topic>Electrochemistry</topic><topic>Enantiomers</topic><topic>Green chemistry</topic><topic>Organic chemistry</topic><topic>Oxidants</topic><topic>Oxidizing agents</topic><topic>Phosphine</topic><topic>Phosphines</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Tao</creatorcontrib><creatorcontrib>Zhang, Wangqin</creatorcontrib><creatorcontrib>Xu, Chao</creatorcontrib><creatorcontrib>Xu, Zhenhui</creatorcontrib><creatorcontrib>Song, Dingguo</creatorcontrib><creatorcontrib>Qian, Wei</creatorcontrib><creatorcontrib>Lu, Gang</creatorcontrib><creatorcontrib>Zhang, Chang-Jun</creatorcontrib><creatorcontrib>Zhong, Weihui</creatorcontrib><creatorcontrib>Ling, Fei</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Environment Abstracts</collection><collection>Sustainability Science Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Materials Research Database</collection><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Tao</au><au>Zhang, Wangqin</au><au>Xu, Chao</au><au>Xu, Zhenhui</au><au>Song, Dingguo</au><au>Qian, Wei</au><au>Lu, Gang</au><au>Zhang, Chang-Jun</au><au>Zhong, Weihui</au><au>Ling, Fei</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of P-stereogenic cyclicphosphinic amides via electrochemically enabled cobalt-catalyzed enantioselective C–H annulation</atitle><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle><date>2023-05-09</date><risdate>2023</risdate><volume>25</volume><issue>9</issue><spage>3606</spage><epage>3614</epage><pages>3606-3614</pages><issn>1463-9262</issn><eissn>1463-9270</eissn><abstract>The development of an electrochemical process method for the synthesis of P-chiral phosphine derivatives poses a considerable challenge. Here, we present an electricity-driven cobalt-catalyzed enantioselective C–H annulation of arylphosphinic amides and alkynes, which provides rapid access to P-chiral cyclicphosphorus oxides in good yields with excellent enantioselectivities (48–99% yields, 94–>99% ee). The reaction was compatible with aqueous solvents and proceeded efficiently in a shorter reaction time compared with the previous work using oxidants. The process employs a combination of readily available chiral salicyloxazoline and cobalt acetate tetrahydrate as an inexpensive catalyst. Notably, the kinetic resolution process was also achieved with
s
factors up to 347.8. Experimental, kinetic and computational studies on cobalta-electrocatalysis provide insights into the catalyst's working mode.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/D3GC00455D</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0002-4274-912X</orcidid><orcidid>https://orcid.org/0000-0003-0349-2226</orcidid></addata></record> |
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source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
subjects | Acetic acid Alkynes Amides Catalysts Chemical reactions Chemical synthesis Cobalt Cobalt acetates Electrochemistry Enantiomers Green chemistry Organic chemistry Oxidants Oxidizing agents Phosphine Phosphines |
title | Synthesis of P-stereogenic cyclicphosphinic amides via electrochemically enabled cobalt-catalyzed enantioselective C–H annulation |
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