Directing-Group-Assisted C(sp2)–H Arylsulfonylation from Sulfur Dioxide

A straightforward and stereoselective preparation of (Z)-β-alkenyl sulfones through a reaction of N-tosyl acrylamides, 1,4-diazabicyclo[2.2.2]­octane-sulfur dioxide, and aryldiazonium tetrafluoroborates under copper catalysis is accomplished. The direct C­(sp2)–H arylsulfonylation of acrylamides usi...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2020-09, Vol.22 (18), p.7094-7097
Hauptverfasser: Zhu, Tonghao, Wu, Jie
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 7097
container_issue 18
container_start_page 7094
container_title Organic letters
container_volume 22
creator Zhu, Tonghao
Wu, Jie
description A straightforward and stereoselective preparation of (Z)-β-alkenyl sulfones through a reaction of N-tosyl acrylamides, 1,4-diazabicyclo[2.2.2]­octane-sulfur dioxide, and aryldiazonium tetrafluoroborates under copper catalysis is accomplished. The direct C­(sp2)–H arylsulfonylation of acrylamides using sulfur dioxide as the sulfonyl source in the presence of copper trifluoroacetate proceeds smoothly, giving rise to (Z)-β-alkenyl sulfones in good yields. During the reaction process, excellent regio- and stereoselectivities are observed.
doi_str_mv 10.1021/acs.orglett.0c02400
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2438692149</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2438692149</sourcerecordid><originalsourceid>FETCH-LOGICAL-a322t-cdf6d4728191d135e7b002f3fc5621ff01d4eea5fbd0fdbd598cdd9676b90ae93</originalsourceid><addsrcrecordid>eNp9kM1KAzEUhYMoWKtP4GaWdTHtTTI_nWVp7Q8UXKjrkMlPSUknY5IBu_MdfEOfxCktLl3dy7nnXDgfQo8YxhgInnARxs7vrIpxDAJIBnCFBjgnNC0hJ9d_ewG36C6EPQDulWqANgvjlYim2aUr77o2nYVgQlQymY9CS55-vr7Xycwfbeisds3R8mhck2jvDslrL3U-WRj3aaS6Rzea26AeLnOI3pfPb_N1un1ZbeazbcopITEVUhcyK8kUV1himquyBiCaapEXBGsNWGZK8VzXErSsZV5NhZRVURZ1BVxVdIhG57-tdx-dCpEdTBDKWt4o1wVGMjotKoKzk5WercK7ELzSrPXmwP2RYWAncKwHxy7g2AVcn5qcU6fj3nW-6ev8m_gFjxp2Ig</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2438692149</pqid></control><display><type>article</type><title>Directing-Group-Assisted C(sp2)–H Arylsulfonylation from Sulfur Dioxide</title><source>ACS Publications</source><creator>Zhu, Tonghao ; Wu, Jie</creator><creatorcontrib>Zhu, Tonghao ; Wu, Jie</creatorcontrib><description>A straightforward and stereoselective preparation of (Z)-β-alkenyl sulfones through a reaction of N-tosyl acrylamides, 1,4-diazabicyclo[2.2.2]­octane-sulfur dioxide, and aryldiazonium tetrafluoroborates under copper catalysis is accomplished. The direct C­(sp2)–H arylsulfonylation of acrylamides using sulfur dioxide as the sulfonyl source in the presence of copper trifluoroacetate proceeds smoothly, giving rise to (Z)-β-alkenyl sulfones in good yields. During the reaction process, excellent regio- and stereoselectivities are observed.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.0c02400</identifier><language>eng</language><publisher>American Chemical Society</publisher><ispartof>Organic letters, 2020-09, Vol.22 (18), p.7094-7097</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a322t-cdf6d4728191d135e7b002f3fc5621ff01d4eea5fbd0fdbd598cdd9676b90ae93</citedby><cites>FETCH-LOGICAL-a322t-cdf6d4728191d135e7b002f3fc5621ff01d4eea5fbd0fdbd598cdd9676b90ae93</cites><orcidid>0000-0002-0967-6360</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.orglett.0c02400$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.orglett.0c02400$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids></links><search><creatorcontrib>Zhu, Tonghao</creatorcontrib><creatorcontrib>Wu, Jie</creatorcontrib><title>Directing-Group-Assisted C(sp2)–H Arylsulfonylation from Sulfur Dioxide</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>A straightforward and stereoselective preparation of (Z)-β-alkenyl sulfones through a reaction of N-tosyl acrylamides, 1,4-diazabicyclo[2.2.2]­octane-sulfur dioxide, and aryldiazonium tetrafluoroborates under copper catalysis is accomplished. The direct C­(sp2)–H arylsulfonylation of acrylamides using sulfur dioxide as the sulfonyl source in the presence of copper trifluoroacetate proceeds smoothly, giving rise to (Z)-β-alkenyl sulfones in good yields. During the reaction process, excellent regio- and stereoselectivities are observed.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9kM1KAzEUhYMoWKtP4GaWdTHtTTI_nWVp7Q8UXKjrkMlPSUknY5IBu_MdfEOfxCktLl3dy7nnXDgfQo8YxhgInnARxs7vrIpxDAJIBnCFBjgnNC0hJ9d_ewG36C6EPQDulWqANgvjlYim2aUr77o2nYVgQlQymY9CS55-vr7Xycwfbeisds3R8mhck2jvDslrL3U-WRj3aaS6Rzea26AeLnOI3pfPb_N1un1ZbeazbcopITEVUhcyK8kUV1himquyBiCaapEXBGsNWGZK8VzXErSsZV5NhZRVURZ1BVxVdIhG57-tdx-dCpEdTBDKWt4o1wVGMjotKoKzk5WercK7ELzSrPXmwP2RYWAncKwHxy7g2AVcn5qcU6fj3nW-6ev8m_gFjxp2Ig</recordid><startdate>20200918</startdate><enddate>20200918</enddate><creator>Zhu, Tonghao</creator><creator>Wu, Jie</creator><general>American Chemical Society</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-0967-6360</orcidid></search><sort><creationdate>20200918</creationdate><title>Directing-Group-Assisted C(sp2)–H Arylsulfonylation from Sulfur Dioxide</title><author>Zhu, Tonghao ; Wu, Jie</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a322t-cdf6d4728191d135e7b002f3fc5621ff01d4eea5fbd0fdbd598cdd9676b90ae93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhu, Tonghao</creatorcontrib><creatorcontrib>Wu, Jie</creatorcontrib><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhu, Tonghao</au><au>Wu, Jie</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Directing-Group-Assisted C(sp2)–H Arylsulfonylation from Sulfur Dioxide</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2020-09-18</date><risdate>2020</risdate><volume>22</volume><issue>18</issue><spage>7094</spage><epage>7097</epage><pages>7094-7097</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>A straightforward and stereoselective preparation of (Z)-β-alkenyl sulfones through a reaction of N-tosyl acrylamides, 1,4-diazabicyclo[2.2.2]­octane-sulfur dioxide, and aryldiazonium tetrafluoroborates under copper catalysis is accomplished. The direct C­(sp2)–H arylsulfonylation of acrylamides using sulfur dioxide as the sulfonyl source in the presence of copper trifluoroacetate proceeds smoothly, giving rise to (Z)-β-alkenyl sulfones in good yields. During the reaction process, excellent regio- and stereoselectivities are observed.</abstract><pub>American Chemical Society</pub><doi>10.1021/acs.orglett.0c02400</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-0967-6360</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2020-09, Vol.22 (18), p.7094-7097
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_2438692149
source ACS Publications
title Directing-Group-Assisted C(sp2)–H Arylsulfonylation from Sulfur Dioxide
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-06T17%3A41%3A11IST&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=Directing-Group-Assisted%20C(sp2)%E2%80%93H%20Arylsulfonylation%20from%20Sulfur%20Dioxide&rft.jtitle=Organic%20letters&rft.au=Zhu,%20Tonghao&rft.date=2020-09-18&rft.volume=22&rft.issue=18&rft.spage=7094&rft.epage=7097&rft.pages=7094-7097&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.0c02400&rft_dat=%3Cproquest_cross%3E2438692149%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=2438692149&rft_id=info:pmid/&rfr_iscdi=true