An aryl thiol-vinyl azide coupling reaction and a thiol-vinyl azide coupling/cyclization cascade: efficient synthesis of β-ketosulfides and arene-fused 5-methylene-2-pyrrolidinone derivatives

The addition reaction of thiol to vinyl azide has been extensively studied. Variously substituted aryl thiols are all viable for this coupling process. The scope of the other partner is successfully expanded from α-aryl vinyl azide to α-alkyl vinyl azide. A thiol-vinyl azide coupling/cyclization cas...

Full description

Saved in:
Bibliographic Details
Published in:Organic & biomolecular chemistry 2021-06, Vol.19 (23), p.5169-5176
Main Authors: Wang, Yong, Wang, Yu-Jiao, Liang, Xian-Chen, Shen, Mei-Hua, Xu, Hua-Dong, Xu, Defeng
Format: Article
Language:English
Subjects:
Aromatic compounds
Azide
Coupling
NMR
Nuclear magnetic resonance
Substitutes
Thiols
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-c337t-e27067684bd94cfa2cc0e325200779b032019ea28be56a1766589818deeb6a773
cites cdi_FETCH-LOGICAL-c337t-e27067684bd94cfa2cc0e325200779b032019ea28be56a1766589818deeb6a773
container_end_page 5176
container_issue 23
container_start_page 5169
container_title Organic & biomolecular chemistry
container_volume 19
creator Wang, Yong
Wang, Yu-Jiao
Liang, Xian-Chen
Shen, Mei-Hua
Xu, Hua-Dong
Xu, Defeng
description The addition reaction of thiol to vinyl azide has been extensively studied. Variously substituted aryl thiols are all viable for this coupling process. The scope of the other partner is successfully expanded from α-aryl vinyl azide to α-alkyl vinyl azide. A thiol-vinyl azide coupling/cyclization cascade is realized with substituted aryl vinyl azides carrying a 2-methoxycarbonyl group. The value of β-ketosulfide products was demonstrated by its application in S-heterocycle synthesis. A radical addition-fragmentation intermediate of vinyl azide can be intercepted by a neighbouring ester group. β-Ketosulfides could be a convenient platform for S-heterocycle synthesis.
doi_str_mv 10.1039/d1ob00328c
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1039_D1OB00328C</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2541661905</sourcerecordid><originalsourceid>FETCH-LOGICAL-c337t-e27067684bd94cfa2cc0e325200779b032019ea28be56a1766589818deeb6a773</originalsourceid><addsrcrecordid>eNp9kk9vFCEYh4mxse3qxbuGxIsxwfJnBmZ6q2utJk160fOEgXdcKgsrzGwy_Vh-gn4CP1Npt66JB0-8gSc_yO8BoZeMvmdUtCeWxZ5SwRvzBB2xSilCa9E-3c-cHqLjnK8pZa2S1TN0KCoqFK3VEbo9C1in2eNx5aInWxfKrG-cBWzitPEufMcJtBldLGCwWP-HPDGz8e5GP8BGZ6MtnGIYBmcchBHnOYwryC7jOODfv8gPGGOe_FAy8i48QQAyTBksrskaxtXs73c42cwpRe-sCzEAtpDctlyzhfwcHQzaZ3jxuC7Qt0_nX5efyeXVxZfl2SUxQqiRAFdUKtlUvW0rM2huDAXBSzdUqbYv7ZVyQPOmh1pqpqSsm7ZhjQXopVZKLNDbXe4mxZ8T5LFbu2zAex0gTrnjteC8qgUVBX3zD3odpxTK6wpVMSlZWwQt0LsdZVLMOcHQbZJbFxcdo9291-4ju_rw4HVZ4NePkVO_BrtH_4gswKsdkLLZn_79GOIOVdSrkg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2541661905</pqid></control><display><type>article</type><title>An aryl thiol-vinyl azide coupling reaction and a thiol-vinyl azide coupling/cyclization cascade: efficient synthesis of β-ketosulfides and arene-fused 5-methylene-2-pyrrolidinone derivatives</title><source>Royal Society of Chemistry:Jisc Collections:Royal Society of Chemistry Read and Publish 2022-2024 (reading list)</source><creator>Wang, Yong ; Wang, Yu-Jiao ; Liang, Xian-Chen ; Shen, Mei-Hua ; Xu, Hua-Dong ; Xu, Defeng</creator><creatorcontrib>Wang, Yong ; Wang, Yu-Jiao ; Liang, Xian-Chen ; Shen, Mei-Hua ; Xu, Hua-Dong ; Xu, Defeng</creatorcontrib><description>The addition reaction of thiol to vinyl azide has been extensively studied. Variously substituted aryl thiols are all viable for this coupling process. The scope of the other partner is successfully expanded from α-aryl vinyl azide to α-alkyl vinyl azide. A thiol-vinyl azide coupling/cyclization cascade is realized with substituted aryl vinyl azides carrying a 2-methoxycarbonyl group. The value of β-ketosulfide products was demonstrated by its application in S-heterocycle synthesis. A radical addition-fragmentation intermediate of vinyl azide can be intercepted by a neighbouring ester group. β-Ketosulfides could be a convenient platform for S-heterocycle synthesis.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/d1ob00328c</identifier><identifier>PMID: 34037057</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Aromatic compounds ; Azide ; Coupling ; NMR ; Nuclear magnetic resonance ; Substitutes ; Thiols</subject><ispartof>Organic &amp; biomolecular chemistry, 2021-06, Vol.19 (23), p.5169-5176</ispartof><rights>Copyright Royal Society of Chemistry 2021</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c337t-e27067684bd94cfa2cc0e325200779b032019ea28be56a1766589818deeb6a773</citedby><cites>FETCH-LOGICAL-c337t-e27067684bd94cfa2cc0e325200779b032019ea28be56a1766589818deeb6a773</cites><orcidid>0000-0003-4416-2143 ; 0000-0002-4510-3754</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/34037057$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wang, Yong</creatorcontrib><creatorcontrib>Wang, Yu-Jiao</creatorcontrib><creatorcontrib>Liang, Xian-Chen</creatorcontrib><creatorcontrib>Shen, Mei-Hua</creatorcontrib><creatorcontrib>Xu, Hua-Dong</creatorcontrib><creatorcontrib>Xu, Defeng</creatorcontrib><title>An aryl thiol-vinyl azide coupling reaction and a thiol-vinyl azide coupling/cyclization cascade: efficient synthesis of β-ketosulfides and arene-fused 5-methylene-2-pyrrolidinone derivatives</title><title>Organic &amp; biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>The addition reaction of thiol to vinyl azide has been extensively studied. Variously substituted aryl thiols are all viable for this coupling process. The scope of the other partner is successfully expanded from α-aryl vinyl azide to α-alkyl vinyl azide. A thiol-vinyl azide coupling/cyclization cascade is realized with substituted aryl vinyl azides carrying a 2-methoxycarbonyl group. The value of β-ketosulfide products was demonstrated by its application in S-heterocycle synthesis. A radical addition-fragmentation intermediate of vinyl azide can be intercepted by a neighbouring ester group. β-Ketosulfides could be a convenient platform for S-heterocycle synthesis.</description><subject>Aromatic compounds</subject><subject>Azide</subject><subject>Coupling</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Substitutes</subject><subject>Thiols</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNp9kk9vFCEYh4mxse3qxbuGxIsxwfJnBmZ6q2utJk160fOEgXdcKgsrzGwy_Vh-gn4CP1Npt66JB0-8gSc_yO8BoZeMvmdUtCeWxZ5SwRvzBB2xSilCa9E-3c-cHqLjnK8pZa2S1TN0KCoqFK3VEbo9C1in2eNx5aInWxfKrG-cBWzitPEufMcJtBldLGCwWP-HPDGz8e5GP8BGZ6MtnGIYBmcchBHnOYwryC7jOODfv8gPGGOe_FAy8i48QQAyTBksrskaxtXs73c42cwpRe-sCzEAtpDctlyzhfwcHQzaZ3jxuC7Qt0_nX5efyeXVxZfl2SUxQqiRAFdUKtlUvW0rM2huDAXBSzdUqbYv7ZVyQPOmh1pqpqSsm7ZhjQXopVZKLNDbXe4mxZ8T5LFbu2zAex0gTrnjteC8qgUVBX3zD3odpxTK6wpVMSlZWwQt0LsdZVLMOcHQbZJbFxcdo9291-4ju_rw4HVZ4NePkVO_BrtH_4gswKsdkLLZn_79GOIOVdSrkg</recordid><startdate>20210616</startdate><enddate>20210616</enddate><creator>Wang, Yong</creator><creator>Wang, Yu-Jiao</creator><creator>Liang, Xian-Chen</creator><creator>Shen, Mei-Hua</creator><creator>Xu, Hua-Dong</creator><creator>Xu, Defeng</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-4416-2143</orcidid><orcidid>https://orcid.org/0000-0002-4510-3754</orcidid></search><sort><creationdate>20210616</creationdate><title>An aryl thiol-vinyl azide coupling reaction and a thiol-vinyl azide coupling/cyclization cascade: efficient synthesis of β-ketosulfides and arene-fused 5-methylene-2-pyrrolidinone derivatives</title><author>Wang, Yong ; Wang, Yu-Jiao ; Liang, Xian-Chen ; Shen, Mei-Hua ; Xu, Hua-Dong ; Xu, Defeng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c337t-e27067684bd94cfa2cc0e325200779b032019ea28be56a1766589818deeb6a773</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Aromatic compounds</topic><topic>Azide</topic><topic>Coupling</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Substitutes</topic><topic>Thiols</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Yong</creatorcontrib><creatorcontrib>Wang, Yu-Jiao</creatorcontrib><creatorcontrib>Liang, Xian-Chen</creatorcontrib><creatorcontrib>Shen, Mei-Hua</creatorcontrib><creatorcontrib>Xu, Hua-Dong</creatorcontrib><creatorcontrib>Xu, Defeng</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Organic &amp; biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Yong</au><au>Wang, Yu-Jiao</au><au>Liang, Xian-Chen</au><au>Shen, Mei-Hua</au><au>Xu, Hua-Dong</au><au>Xu, Defeng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An aryl thiol-vinyl azide coupling reaction and a thiol-vinyl azide coupling/cyclization cascade: efficient synthesis of β-ketosulfides and arene-fused 5-methylene-2-pyrrolidinone derivatives</atitle><jtitle>Organic &amp; biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2021-06-16</date><risdate>2021</risdate><volume>19</volume><issue>23</issue><spage>5169</spage><epage>5176</epage><pages>5169-5176</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>The addition reaction of thiol to vinyl azide has been extensively studied. Variously substituted aryl thiols are all viable for this coupling process. The scope of the other partner is successfully expanded from α-aryl vinyl azide to α-alkyl vinyl azide. A thiol-vinyl azide coupling/cyclization cascade is realized with substituted aryl vinyl azides carrying a 2-methoxycarbonyl group. The value of β-ketosulfide products was demonstrated by its application in S-heterocycle synthesis. A radical addition-fragmentation intermediate of vinyl azide can be intercepted by a neighbouring ester group. β-Ketosulfides could be a convenient platform for S-heterocycle synthesis.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>34037057</pmid><doi>10.1039/d1ob00328c</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0003-4416-2143</orcidid><orcidid>https://orcid.org/0000-0002-4510-3754</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1477-0520
ispartof Organic & biomolecular chemistry, 2021-06, Vol.19 (23), p.5169-5176
issn 1477-0520
1477-0539
language eng
recordid cdi_crossref_primary_10_1039_D1OB00328C
source Royal Society of Chemistry:Jisc Collections:Royal Society of Chemistry Read and Publish 2022-2024 (reading list)
subjects Aromatic compounds
Azide
Coupling
NMR
Nuclear magnetic resonance
Substitutes
Thiols
title An aryl thiol-vinyl azide coupling reaction and a thiol-vinyl azide coupling/cyclization cascade: efficient synthesis of β-ketosulfides and arene-fused 5-methylene-2-pyrrolidinone derivatives
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-29T15%3A53%3A19IST&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=An%20aryl%20thiol-vinyl%20azide%20coupling%20reaction%20and%20a%20thiol-vinyl%20azide%20coupling/cyclization%20cascade:%20efficient%20synthesis%20of%20%CE%B2-ketosulfides%20and%20arene-fused%205-methylene-2-pyrrolidinone%20derivatives&rft.jtitle=Organic%20&%20biomolecular%20chemistry&rft.au=Wang,%20Yong&rft.date=2021-06-16&rft.volume=19&rft.issue=23&rft.spage=5169&rft.epage=5176&rft.pages=5169-5176&rft.issn=1477-0520&rft.eissn=1477-0539&rft_id=info:doi/10.1039/d1ob00328c&rft_dat=%3Cproquest_cross%3E2541661905%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c337t-e27067684bd94cfa2cc0e325200779b032019ea28be56a1766589818deeb6a773%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2541661905&rft_id=info:pmid/34037057&rfr_iscdi=true