Copper-Catalyzed Regio- and Stereoselective Sulfonylation of Alkynyl Imines with Sulfonyl Hydrazides: Access to (E)‑β-Sulfonyl Enones
A copper-catalyzed sulfonylation of alkynyl imines with sulfonyl hydrazides has been developed, which exhibited excellent regio- and stereoselectivity and furnished a series of (E)-β-sulfonyl enones in moderate to good yields. Mechanistic studies suggest that this strategy goes through a radical pro...
Gespeichert in:
Veröffentlicht in: | Journal of organic chemistry 2022-10, Vol.87 (19), p.13322-13330 |
---|---|
Hauptverfasser: | , , , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
container_end_page | 13330 |
---|---|
container_issue | 19 |
container_start_page | 13322 |
container_title | Journal of organic chemistry |
container_volume | 87 |
creator | Chen, Rongxiang Li, Shaozhu Zhang, Jinju Cao, Jing Wang, Kai-Kai Meng, Tuanjie Liu, Lantao |
description | A copper-catalyzed sulfonylation of alkynyl imines with sulfonyl hydrazides has been developed, which exhibited excellent regio- and stereoselectivity and furnished a series of (E)-β-sulfonyl enones in moderate to good yields. Mechanistic studies suggest that this strategy goes through a radical process. |
doi_str_mv | 10.1021/acs.joc.2c01192 |
format | Article |
fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2716526985</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2716526985</sourcerecordid><originalsourceid>FETCH-LOGICAL-a240t-c2116151274d46308087ace2e114ebeb1c8c934395999a62a62347ffabc05eec3</originalsourceid><addsrcrecordid>eNp1kM9KAzEQh4MoWKtnrzlWZNsku9k_3kqptlAQrJ6XNDurW7ebNckq25NHr76KD-JD-CRGtvTmMDCEfL-B-RA6p2RICaMjIc1wreSQSUJpwg5Qj3JGvDAhwSHqEcKY57PQP0YnxqyJK855D31MVF2D9ibCirLdQobv4LFQHhZVhpcWNCgDJUhbvAJeNmWuqrYUtlAVVjkel8-te-P5pqjA4LfCPu0hPGszLbZFBuYKj6UEY7BVeDC9-Hn__P7y9ty0Ui58io5yURo4280-erie3k9m3uL2Zj4ZLzzBAmI9ySgNKacsCrIg9ElM4khIYEBpACtYURnLxA_8hCdJIkLm2g-iPBcrSTiA9Pto0O2ttXppwNh0UxgJZSkqUI1JWURDzsIk5g4ddajUyhgNeVrrYiN0m1KS_jlPnfPUOU93zl3iskt0H42u3Cn_0r_RCId8</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2716526985</pqid></control><display><type>article</type><title>Copper-Catalyzed Regio- and Stereoselective Sulfonylation of Alkynyl Imines with Sulfonyl Hydrazides: Access to (E)‑β-Sulfonyl Enones</title><source>American Chemical Society Journals</source><creator>Chen, Rongxiang ; Li, Shaozhu ; Zhang, Jinju ; Cao, Jing ; Wang, Kai-Kai ; Meng, Tuanjie ; Liu, Lantao</creator><creatorcontrib>Chen, Rongxiang ; Li, Shaozhu ; Zhang, Jinju ; Cao, Jing ; Wang, Kai-Kai ; Meng, Tuanjie ; Liu, Lantao</creatorcontrib><description>A copper-catalyzed sulfonylation of alkynyl imines with sulfonyl hydrazides has been developed, which exhibited excellent regio- and stereoselectivity and furnished a series of (E)-β-sulfonyl enones in moderate to good yields. Mechanistic studies suggest that this strategy goes through a radical process.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.2c01192</identifier><language>eng</language><publisher>American Chemical Society</publisher><ispartof>Journal of organic chemistry, 2022-10, Vol.87 (19), p.13322-13330</ispartof><rights>2022 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a240t-c2116151274d46308087ace2e114ebeb1c8c934395999a62a62347ffabc05eec3</citedby><cites>FETCH-LOGICAL-a240t-c2116151274d46308087ace2e114ebeb1c8c934395999a62a62347ffabc05eec3</cites><orcidid>0000-0002-6107-1019 ; 0000-0002-8025-7222 ; 0000-0002-3843-2074</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.2c01192$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.joc.2c01192$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids></links><search><creatorcontrib>Chen, Rongxiang</creatorcontrib><creatorcontrib>Li, Shaozhu</creatorcontrib><creatorcontrib>Zhang, Jinju</creatorcontrib><creatorcontrib>Cao, Jing</creatorcontrib><creatorcontrib>Wang, Kai-Kai</creatorcontrib><creatorcontrib>Meng, Tuanjie</creatorcontrib><creatorcontrib>Liu, Lantao</creatorcontrib><title>Copper-Catalyzed Regio- and Stereoselective Sulfonylation of Alkynyl Imines with Sulfonyl Hydrazides: Access to (E)‑β-Sulfonyl Enones</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>A copper-catalyzed sulfonylation of alkynyl imines with sulfonyl hydrazides has been developed, which exhibited excellent regio- and stereoselectivity and furnished a series of (E)-β-sulfonyl enones in moderate to good yields. Mechanistic studies suggest that this strategy goes through a radical process.</description><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNp1kM9KAzEQh4MoWKtnrzlWZNsku9k_3kqptlAQrJ6XNDurW7ebNckq25NHr76KD-JD-CRGtvTmMDCEfL-B-RA6p2RICaMjIc1wreSQSUJpwg5Qj3JGvDAhwSHqEcKY57PQP0YnxqyJK855D31MVF2D9ibCirLdQobv4LFQHhZVhpcWNCgDJUhbvAJeNmWuqrYUtlAVVjkel8-te-P5pqjA4LfCPu0hPGszLbZFBuYKj6UEY7BVeDC9-Hn__P7y9ty0Ui58io5yURo4280-erie3k9m3uL2Zj4ZLzzBAmI9ySgNKacsCrIg9ElM4khIYEBpACtYURnLxA_8hCdJIkLm2g-iPBcrSTiA9Pto0O2ttXppwNh0UxgJZSkqUI1JWURDzsIk5g4ddajUyhgNeVrrYiN0m1KS_jlPnfPUOU93zl3iskt0H42u3Cn_0r_RCId8</recordid><startdate>20221007</startdate><enddate>20221007</enddate><creator>Chen, Rongxiang</creator><creator>Li, Shaozhu</creator><creator>Zhang, Jinju</creator><creator>Cao, Jing</creator><creator>Wang, Kai-Kai</creator><creator>Meng, Tuanjie</creator><creator>Liu, Lantao</creator><general>American Chemical Society</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-6107-1019</orcidid><orcidid>https://orcid.org/0000-0002-8025-7222</orcidid><orcidid>https://orcid.org/0000-0002-3843-2074</orcidid></search><sort><creationdate>20221007</creationdate><title>Copper-Catalyzed Regio- and Stereoselective Sulfonylation of Alkynyl Imines with Sulfonyl Hydrazides: Access to (E)‑β-Sulfonyl Enones</title><author>Chen, Rongxiang ; Li, Shaozhu ; Zhang, Jinju ; Cao, Jing ; Wang, Kai-Kai ; Meng, Tuanjie ; Liu, Lantao</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a240t-c2116151274d46308087ace2e114ebeb1c8c934395999a62a62347ffabc05eec3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chen, Rongxiang</creatorcontrib><creatorcontrib>Li, Shaozhu</creatorcontrib><creatorcontrib>Zhang, Jinju</creatorcontrib><creatorcontrib>Cao, Jing</creatorcontrib><creatorcontrib>Wang, Kai-Kai</creatorcontrib><creatorcontrib>Meng, Tuanjie</creatorcontrib><creatorcontrib>Liu, Lantao</creatorcontrib><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>Chen, Rongxiang</au><au>Li, Shaozhu</au><au>Zhang, Jinju</au><au>Cao, Jing</au><au>Wang, Kai-Kai</au><au>Meng, Tuanjie</au><au>Liu, Lantao</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper-Catalyzed Regio- and Stereoselective Sulfonylation of Alkynyl Imines with Sulfonyl Hydrazides: Access to (E)‑β-Sulfonyl Enones</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2022-10-07</date><risdate>2022</risdate><volume>87</volume><issue>19</issue><spage>13322</spage><epage>13330</epage><pages>13322-13330</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>A copper-catalyzed sulfonylation of alkynyl imines with sulfonyl hydrazides has been developed, which exhibited excellent regio- and stereoselectivity and furnished a series of (E)-β-sulfonyl enones in moderate to good yields. Mechanistic studies suggest that this strategy goes through a radical process.</abstract><pub>American Chemical Society</pub><doi>10.1021/acs.joc.2c01192</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0002-6107-1019</orcidid><orcidid>https://orcid.org/0000-0002-8025-7222</orcidid><orcidid>https://orcid.org/0000-0002-3843-2074</orcidid></addata></record> |
fulltext | fulltext |
identifier | ISSN: 0022-3263 |
ispartof | Journal of organic chemistry, 2022-10, Vol.87 (19), p.13322-13330 |
issn | 0022-3263 1520-6904 |
language | eng |
recordid | cdi_proquest_miscellaneous_2716526985 |
source | American Chemical Society Journals |
title | Copper-Catalyzed Regio- and Stereoselective Sulfonylation of Alkynyl Imines with Sulfonyl Hydrazides: Access to (E)‑β-Sulfonyl Enones |
url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-22T08%3A16%3A36IST&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=Copper-Catalyzed%20Regio-%20and%20Stereoselective%20Sulfonylation%20of%20Alkynyl%20Imines%20with%20Sulfonyl%20Hydrazides:%20Access%20to%20(E)%E2%80%91%CE%B2-Sulfonyl%20Enones&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Chen,%20Rongxiang&rft.date=2022-10-07&rft.volume=87&rft.issue=19&rft.spage=13322&rft.epage=13330&rft.pages=13322-13330&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.2c01192&rft_dat=%3Cproquest_cross%3E2716526985%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=2716526985&rft_id=info:pmid/&rfr_iscdi=true |