Generation of [beta]-Halo Vinylsulfones through a Multicomponent Reaction with Insertion of Sulfur Dioxide

A four-component reaction of terminal alkynes, aryldiazonium tetrafluoroborates, sulfur dioxide surrogate of DABCO(SO2)2, and potassium halide in the presence of copper(I) chloride (10mol%) gives rise to [beta]-halo vinylsulfones with good stereoselectivity. The vicinal difunctionalization of alkyne...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Chemistry : a European journal 2017-05, Vol.23 (29), p.6996
Hauptverfasser:	Xiang, Yuanchao, Kuang, Yunyan, Wu, Jie
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkynes Chemistry Copper chloride Halogenation Insertion Stereoselectivity Sulfur Sulfur dioxide
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

container_end_page
container_issue	29
container_start_page	6996
container_title	Chemistry : a European journal
container_volume	23
creator	Xiang, Yuanchao Kuang, Yunyan Wu, Jie
description	A four-component reaction of terminal alkynes, aryldiazonium tetrafluoroborates, sulfur dioxide surrogate of DABCO(SO2)2, and potassium halide in the presence of copper(I) chloride (10mol%) gives rise to [beta]-halo vinylsulfones with good stereoselectivity. The vicinal difunctionalization of alkynes through sulfonylation and halogenation with the insertion of sulfur dioxide works efficiently. A plausible mechanism is proposed, which includes a radical process.
doi_str_mv	10.1002/chem.201701465
format	Article
fullrecord	<record><control><sourceid>proquest</sourceid><recordid>TN_cdi_proquest_journals_1901454857</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1901454857</sourcerecordid><originalsourceid>FETCH-proquest_journals_19014548573</originalsourceid><addsrcrecordid>eNqNjztPxDAQhC0EEuHRUq9EnWMdxwmpeR0FDSAahE4mbIgjn_fwQ8C_vwhBTzXSzHwjjRAnEhcSsTrrR1ovKpQtyrrRO6KQupKlahu9Kwrs6rZstOr2xUGMEyJ2jVKFmG7IUzDJsgce4PmVknkpl8YxPFn_7WJ2A3uKkMbA-X0EA3fZJdvzejP7PsE9mf4H_7RphFsfKfytPcxwDnBp-cu-0ZHYG4yLdPyrh-L0-urxYlluAn9kimk1cQ5-jlaymz_o-ly36n-tLYWQT7A</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1901454857</pqid></control><display><type>article</type><title>Generation of [beta]-Halo Vinylsulfones through a Multicomponent Reaction with Insertion of Sulfur Dioxide</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Xiang, Yuanchao ; Kuang, Yunyan ; Wu, Jie</creator><creatorcontrib>Xiang, Yuanchao ; Kuang, Yunyan ; Wu, Jie</creatorcontrib><description>A four-component reaction of terminal alkynes, aryldiazonium tetrafluoroborates, sulfur dioxide surrogate of DABCO(SO2)2, and potassium halide in the presence of copper(I) chloride (10mol%) gives rise to [beta]-halo vinylsulfones with good stereoselectivity. The vicinal difunctionalization of alkynes through sulfonylation and halogenation with the insertion of sulfur dioxide works efficiently. A plausible mechanism is proposed, which includes a radical process.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201701465</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Alkynes ; Chemistry ; Copper chloride ; Halogenation ; Insertion ; Stereoselectivity ; Sulfur ; Sulfur dioxide</subject><ispartof>Chemistry : a European journal, 2017-05, Vol.23 (29), p.6996</ispartof><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Xiang, Yuanchao</creatorcontrib><creatorcontrib>Kuang, Yunyan</creatorcontrib><creatorcontrib>Wu, Jie</creatorcontrib><title>Generation of [beta]-Halo Vinylsulfones through a Multicomponent Reaction with Insertion of Sulfur Dioxide</title><title>Chemistry : a European journal</title><description>A four-component reaction of terminal alkynes, aryldiazonium tetrafluoroborates, sulfur dioxide surrogate of DABCO(SO2)2, and potassium halide in the presence of copper(I) chloride (10mol%) gives rise to [beta]-halo vinylsulfones with good stereoselectivity. The vicinal difunctionalization of alkynes through sulfonylation and halogenation with the insertion of sulfur dioxide works efficiently. A plausible mechanism is proposed, which includes a radical process.</description><subject>Alkynes</subject><subject>Chemistry</subject><subject>Copper chloride</subject><subject>Halogenation</subject><subject>Insertion</subject><subject>Stereoselectivity</subject><subject>Sulfur</subject><subject>Sulfur dioxide</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqNjztPxDAQhC0EEuHRUq9EnWMdxwmpeR0FDSAahE4mbIgjn_fwQ8C_vwhBTzXSzHwjjRAnEhcSsTrrR1ovKpQtyrrRO6KQupKlahu9Kwrs6rZstOr2xUGMEyJ2jVKFmG7IUzDJsgce4PmVknkpl8YxPFn_7WJ2A3uKkMbA-X0EA3fZJdvzejP7PsE9mf4H_7RphFsfKfytPcxwDnBp-cu-0ZHYG4yLdPyrh-L0-urxYlluAn9kimk1cQ5-jlaymz_o-ly36n-tLYWQT7A</recordid><startdate>20170523</startdate><enddate>20170523</enddate><creator>Xiang, Yuanchao</creator><creator>Kuang, Yunyan</creator><creator>Wu, Jie</creator><general>Wiley Subscription Services, Inc</general><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope></search><sort><creationdate>20170523</creationdate><title>Generation of [beta]-Halo Vinylsulfones through a Multicomponent Reaction with Insertion of Sulfur Dioxide</title><author>Xiang, Yuanchao ; Kuang, Yunyan ; Wu, Jie</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-proquest_journals_19014548573</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Alkynes</topic><topic>Chemistry</topic><topic>Copper chloride</topic><topic>Halogenation</topic><topic>Insertion</topic><topic>Stereoselectivity</topic><topic>Sulfur</topic><topic>Sulfur dioxide</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Xiang, Yuanchao</creatorcontrib><creatorcontrib>Kuang, Yunyan</creatorcontrib><creatorcontrib>Wu, Jie</creatorcontrib><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Xiang, Yuanchao</au><au>Kuang, Yunyan</au><au>Wu, Jie</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Generation of [beta]-Halo Vinylsulfones through a Multicomponent Reaction with Insertion of Sulfur Dioxide</atitle><jtitle>Chemistry : a European journal</jtitle><date>2017-05-23</date><risdate>2017</risdate><volume>23</volume><issue>29</issue><spage>6996</spage><pages>6996-</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>A four-component reaction of terminal alkynes, aryldiazonium tetrafluoroborates, sulfur dioxide surrogate of DABCO(SO2)2, and potassium halide in the presence of copper(I) chloride (10mol%) gives rise to [beta]-halo vinylsulfones with good stereoselectivity. The vicinal difunctionalization of alkynes through sulfonylation and halogenation with the insertion of sulfur dioxide works efficiently. A plausible mechanism is proposed, which includes a radical process.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/chem.201701465</doi></addata></record>
fulltext	fulltext
identifier	ISSN: 0947-6539
ispartof	Chemistry : a European journal, 2017-05, Vol.23 (29), p.6996
issn	0947-6539 1521-3765
language	eng
recordid	cdi_proquest_journals_1901454857
source	Wiley Online Library Journals Frontfile Complete
subjects	Alkynes Chemistry Copper chloride Halogenation Insertion Stereoselectivity Sulfur Sulfur dioxide
title	Generation of [beta]-Halo Vinylsulfones through a Multicomponent Reaction with Insertion of Sulfur Dioxide
url	https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-20T21%3A10%3A50IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Generation%20of%20%5Bbeta%5D-Halo%20Vinylsulfones%20through%20a%20Multicomponent%20Reaction%20with%20Insertion%20of%20Sulfur%20Dioxide&rft.jtitle=Chemistry%20:%20a%20European%20journal&rft.au=Xiang,%20Yuanchao&rft.date=2017-05-23&rft.volume=23&rft.issue=29&rft.spage=6996&rft.pages=6996-&rft.issn=0947-6539&rft.eissn=1521-3765&rft_id=info:doi/10.1002/chem.201701465&rft_dat=%3Cproquest%3E1901454857%3C/proquest%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1901454857&rft_id=info:pmid/&rfr_iscdi=true