An operationally simple approach to (E)-α-halo vinyl sulfides and their applications for accessing stereodefined trisubstituted alkenes

An operationally simple and practical protocol for the synthesis of (E)-α-halo vinyl sulfides has been achieved via a highly regio- and stereoselective hydrohalogenation of alkynyl thioethers using lithium halides in HOAc or propionic acid at room temperature. It permits the formation of (E)-α-chlor...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Organic & biomolecular chemistry 2013-04, Vol.11 (13), p.2175-2185
Hauptverfasser:	Yang, Zhaozhen, Chen, Xiaoyi, Kong, Wei, Xia, Siyuan, Zheng, Renwei, Luo, Fang, Zhu, Gangguo
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkenes - chemical synthesis Alkenes - chemistry Alkynes - chemistry Hydrocarbons, Halogenated - chemical synthesis Hydrocarbons, Halogenated - chemistry Molecular Structure Stereoisomerism Sulfhydryl Compounds - chemistry Sulfides - chemical synthesis Sulfides - chemistry
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

container_end_page	2185
container_issue	13
container_start_page	2175
container_title	Organic & biomolecular chemistry
container_volume	11
creator	Yang, Zhaozhen Chen, Xiaoyi Kong, Wei Xia, Siyuan Zheng, Renwei Luo, Fang Zhu, Gangguo
description	An operationally simple and practical protocol for the synthesis of (E)-α-halo vinyl sulfides has been achieved via a highly regio- and stereoselective hydrohalogenation of alkynyl thioethers using lithium halides in HOAc or propionic acid at room temperature. It permits the formation of (E)-α-chloro and (E)-α-bromo vinyl sulfides in satisfactory yields with good to excellent stereoselectivities. Moreover, this work results in a new method for the assembly of stereodefined (E)- or (Z)-trisubstituted alkenes featuring the first coupling of the C-X bond of (E)-α-halo vinyl sulfides followed by a subsequent Ni-catalyzed coupling of the C-S bond with Grignard reagents.
doi_str_mv	10.1039/c3ob27307e
format	Article
fullrecord	<record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1315629282</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1315629282</sourcerecordid><originalsourceid>FETCH-LOGICAL-c287t-6cf4066bc382e7b9b38bf180c42dd92642b5f5e3c1414e10c5ef2c566ca2a1143</originalsourceid><addsrcrecordid>eNpFkMtO3DAUhq0KVAbaDQ-AvJwihfqWOFmOEIVKI3VD15HjHHcMnjj4OEjzBn0dXqTPRKZM6epc9J1POj8h55xdcSabr1bGTmjJNHwgC660Llgpm6P3XrATcor4wBhvdKU-khMhFZNaywX5vRpoHCGZ7ONgQthR9NsxADXjmKKxG5ojXd58Kf68FBsTIn32wy5QnILzPSA1Q0_zBnzaHwRv_3qQujgvrAVEP_yimCFB7MH5AWY8eZw6zD5PeR5NeIQB8BM5diYgfD7UM_Lz28399V2x_nH7_Xq1LqyodS4q6xSrqs7KWoDumk7WneM1s0r0fSMqJbrSlSAtV1wBZ7YEJ2xZVdYIw7mSZ2T55p3fe5oAc7v1aCEEM0CcsOWSl5VoRC1m9PINtSkiJnDtmPzWpF3LWbtPvv2f_AxfHLxTt4X-Hf0XtXwFpJKCRA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1315629282</pqid></control><display><type>article</type><title>An operationally simple approach to (E)-α-halo vinyl sulfides and their applications for accessing stereodefined trisubstituted alkenes</title><source>MEDLINE</source><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Yang, Zhaozhen ; Chen, Xiaoyi ; Kong, Wei ; Xia, Siyuan ; Zheng, Renwei ; Luo, Fang ; Zhu, Gangguo</creator><creatorcontrib>Yang, Zhaozhen ; Chen, Xiaoyi ; Kong, Wei ; Xia, Siyuan ; Zheng, Renwei ; Luo, Fang ; Zhu, Gangguo</creatorcontrib><description>An operationally simple and practical protocol for the synthesis of (E)-α-halo vinyl sulfides has been achieved via a highly regio- and stereoselective hydrohalogenation of alkynyl thioethers using lithium halides in HOAc or propionic acid at room temperature. It permits the formation of (E)-α-chloro and (E)-α-bromo vinyl sulfides in satisfactory yields with good to excellent stereoselectivities. Moreover, this work results in a new method for the assembly of stereodefined (E)- or (Z)-trisubstituted alkenes featuring the first coupling of the C-X bond of (E)-α-halo vinyl sulfides followed by a subsequent Ni-catalyzed coupling of the C-S bond with Grignard reagents.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/c3ob27307e</identifier><identifier>PMID: 23403773</identifier><language>eng</language><publisher>England</publisher><subject>Alkenes - chemical synthesis ; Alkenes - chemistry ; Alkynes - chemistry ; Hydrocarbons, Halogenated - chemical synthesis ; Hydrocarbons, Halogenated - chemistry ; Molecular Structure ; Stereoisomerism ; Sulfhydryl Compounds - chemistry ; Sulfides - chemical synthesis ; Sulfides - chemistry</subject><ispartof>Organic & biomolecular chemistry, 2013-04, Vol.11 (13), p.2175-2185</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c287t-6cf4066bc382e7b9b38bf180c42dd92642b5f5e3c1414e10c5ef2c566ca2a1143</citedby><cites>FETCH-LOGICAL-c287t-6cf4066bc382e7b9b38bf180c42dd92642b5f5e3c1414e10c5ef2c566ca2a1143</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,27905,27906</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23403773$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yang, Zhaozhen</creatorcontrib><creatorcontrib>Chen, Xiaoyi</creatorcontrib><creatorcontrib>Kong, Wei</creatorcontrib><creatorcontrib>Xia, Siyuan</creatorcontrib><creatorcontrib>Zheng, Renwei</creatorcontrib><creatorcontrib>Luo, Fang</creatorcontrib><creatorcontrib>Zhu, Gangguo</creatorcontrib><title>An operationally simple approach to (E)-α-halo vinyl sulfides and their applications for accessing stereodefined trisubstituted alkenes</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>An operationally simple and practical protocol for the synthesis of (E)-α-halo vinyl sulfides has been achieved via a highly regio- and stereoselective hydrohalogenation of alkynyl thioethers using lithium halides in HOAc or propionic acid at room temperature. It permits the formation of (E)-α-chloro and (E)-α-bromo vinyl sulfides in satisfactory yields with good to excellent stereoselectivities. Moreover, this work results in a new method for the assembly of stereodefined (E)- or (Z)-trisubstituted alkenes featuring the first coupling of the C-X bond of (E)-α-halo vinyl sulfides followed by a subsequent Ni-catalyzed coupling of the C-S bond with Grignard reagents.</description><subject>Alkenes - chemical synthesis</subject><subject>Alkenes - chemistry</subject><subject>Alkynes - chemistry</subject><subject>Hydrocarbons, Halogenated - chemical synthesis</subject><subject>Hydrocarbons, Halogenated - chemistry</subject><subject>Molecular Structure</subject><subject>Stereoisomerism</subject><subject>Sulfhydryl Compounds - chemistry</subject><subject>Sulfides - chemical synthesis</subject><subject>Sulfides - chemistry</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkMtO3DAUhq0KVAbaDQ-AvJwihfqWOFmOEIVKI3VD15HjHHcMnjj4OEjzBn0dXqTPRKZM6epc9J1POj8h55xdcSabr1bGTmjJNHwgC660Llgpm6P3XrATcor4wBhvdKU-khMhFZNaywX5vRpoHCGZ7ONgQthR9NsxADXjmKKxG5ojXd58Kf68FBsTIn32wy5QnILzPSA1Q0_zBnzaHwRv_3qQujgvrAVEP_yimCFB7MH5AWY8eZw6zD5PeR5NeIQB8BM5diYgfD7UM_Lz28399V2x_nH7_Xq1LqyodS4q6xSrqs7KWoDumk7WneM1s0r0fSMqJbrSlSAtV1wBZ7YEJ2xZVdYIw7mSZ2T55p3fe5oAc7v1aCEEM0CcsOWSl5VoRC1m9PINtSkiJnDtmPzWpF3LWbtPvv2f_AxfHLxTt4X-Hf0XtXwFpJKCRA</recordid><startdate>20130407</startdate><enddate>20130407</enddate><creator>Yang, Zhaozhen</creator><creator>Chen, Xiaoyi</creator><creator>Kong, Wei</creator><creator>Xia, Siyuan</creator><creator>Zheng, Renwei</creator><creator>Luo, Fang</creator><creator>Zhu, Gangguo</creator><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20130407</creationdate><title>An operationally simple approach to (E)-α-halo vinyl sulfides and their applications for accessing stereodefined trisubstituted alkenes</title><author>Yang, Zhaozhen ; Chen, Xiaoyi ; Kong, Wei ; Xia, Siyuan ; Zheng, Renwei ; Luo, Fang ; Zhu, Gangguo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c287t-6cf4066bc382e7b9b38bf180c42dd92642b5f5e3c1414e10c5ef2c566ca2a1143</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Alkenes - chemical synthesis</topic><topic>Alkenes - chemistry</topic><topic>Alkynes - chemistry</topic><topic>Hydrocarbons, Halogenated - chemical synthesis</topic><topic>Hydrocarbons, Halogenated - chemistry</topic><topic>Molecular Structure</topic><topic>Stereoisomerism</topic><topic>Sulfhydryl Compounds - chemistry</topic><topic>Sulfides - chemical synthesis</topic><topic>Sulfides - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yang, Zhaozhen</creatorcontrib><creatorcontrib>Chen, Xiaoyi</creatorcontrib><creatorcontrib>Kong, Wei</creatorcontrib><creatorcontrib>Xia, Siyuan</creatorcontrib><creatorcontrib>Zheng, Renwei</creatorcontrib><creatorcontrib>Luo, Fang</creatorcontrib><creatorcontrib>Zhu, Gangguo</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yang, Zhaozhen</au><au>Chen, Xiaoyi</au><au>Kong, Wei</au><au>Xia, Siyuan</au><au>Zheng, Renwei</au><au>Luo, Fang</au><au>Zhu, Gangguo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An operationally simple approach to (E)-α-halo vinyl sulfides and their applications for accessing stereodefined trisubstituted alkenes</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2013-04-07</date><risdate>2013</risdate><volume>11</volume><issue>13</issue><spage>2175</spage><epage>2185</epage><pages>2175-2185</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>An operationally simple and practical protocol for the synthesis of (E)-α-halo vinyl sulfides has been achieved via a highly regio- and stereoselective hydrohalogenation of alkynyl thioethers using lithium halides in HOAc or propionic acid at room temperature. It permits the formation of (E)-α-chloro and (E)-α-bromo vinyl sulfides in satisfactory yields with good to excellent stereoselectivities. Moreover, this work results in a new method for the assembly of stereodefined (E)- or (Z)-trisubstituted alkenes featuring the first coupling of the C-X bond of (E)-α-halo vinyl sulfides followed by a subsequent Ni-catalyzed coupling of the C-S bond with Grignard reagents.</abstract><cop>England</cop><pmid>23403773</pmid><doi>10.1039/c3ob27307e</doi><tpages>11</tpages></addata></record>
fulltext	fulltext
identifier	ISSN: 1477-0520
ispartof	Organic & biomolecular chemistry, 2013-04, Vol.11 (13), p.2175-2185
issn	1477-0520 1477-0539
language	eng
recordid	cdi_proquest_miscellaneous_1315629282
source	MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects	Alkenes - chemical synthesis Alkenes - chemistry Alkynes - chemistry Hydrocarbons, Halogenated - chemical synthesis Hydrocarbons, Halogenated - chemistry Molecular Structure Stereoisomerism Sulfhydryl Compounds - chemistry Sulfides - chemical synthesis Sulfides - chemistry
title	An operationally simple approach to (E)-α-halo vinyl sulfides and their applications for accessing stereodefined trisubstituted alkenes
url	https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-19T17%3A09%3A38IST&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%20operationally%20simple%20approach%20to%20(E)-%CE%B1-halo%20vinyl%20sulfides%20and%20their%20applications%20for%20accessing%20stereodefined%20trisubstituted%20alkenes&rft.jtitle=Organic%20&%20biomolecular%20chemistry&rft.au=Yang,%20Zhaozhen&rft.date=2013-04-07&rft.volume=11&rft.issue=13&rft.spage=2175&rft.epage=2185&rft.pages=2175-2185&rft.issn=1477-0520&rft.eissn=1477-0539&rft_id=info:doi/10.1039/c3ob27307e&rft_dat=%3Cproquest_cross%3E1315629282%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=1315629282&rft_id=info:pmid/23403773&rfr_iscdi=true