A Platform for the Synthesis of Diverse Phosphonyl and Thiofunctionalized Sulfoxonium Ylides

A practical strategy for the construction of diverse phosphonyl and thiofunctionalized sulfoxonium ylides via controllable monofunctionalization of hybrid I(III)/S(VI) ylides is presented. This process allows efficient P–H insertion of I(III)/S(VI) ylides under Cu catalysis, enabling the synthesis o...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2024-07, Vol.26 (27), p.5811-5816
Main Authors: Zou, Wen-Xuan, Hu, Qiong, Shen, Dan-Ting, Wu, Wen-Rong, Wei, Jiaohang, Yang, Zi-Feng, Bao, Mei-Zhu, Liu, Xiang, Zhang, Shang-Shi
Format: Article
Language:English
Subjects:
catalytic activity
derivatization
utilities
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by
cites cdi_FETCH-LOGICAL-a258t-abb388ad399cf7461762efc58cf91b2acf65b11d1e7f7f87f52346c466891f2d3
container_end_page 5816
container_issue 27
container_start_page 5811
container_title Organic letters
container_volume 26
creator Zou, Wen-Xuan
Hu, Qiong
Shen, Dan-Ting
Wu, Wen-Rong
Wei, Jiaohang
Yang, Zi-Feng
Bao, Mei-Zhu
Liu, Xiang
Zhang, Shang-Shi
description A practical strategy for the construction of diverse phosphonyl and thiofunctionalized sulfoxonium ylides via controllable monofunctionalization of hybrid I(III)/S(VI) ylides is presented. This process allows efficient P–H insertion of I(III)/S(VI) ylides under Cu catalysis, enabling the synthesis of phosphonyl sulfoxonium ylides, whereas reaction with sulfur-containing reagents including AgSCF3, KSC­(S)­OR, and KSCN under mild conditions resulted in α-trifluoromethylthiolation, dithiocarbanation, and thiocyanation of sulfoxonium ylides accordingly. Of note, wide substrate compatibility (108 examples), excellent efficiency (up to 99% yield), gram-scale experiments, and various product derivatizations highlight the synthetic utility of this protocol.
doi_str_mv 10.1021/acs.orglett.4c02000
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_3073235189</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3153643932</sourcerecordid><originalsourceid>FETCH-LOGICAL-a258t-abb388ad399cf7461762efc58cf91b2acf65b11d1e7f7f87f52346c466891f2d3</originalsourceid><addsrcrecordid>eNqFkU1LAzEQhoMoVqu_QJAcvWybj_3KsdRPKFhoPQjCks0mNiW7qcmuWH-9KV171MvMMDzvDDMvAFcYjTAieMyFH1n3bmTbjmKBCELoCJzhhNAoQwk5PtQpGoBz79cI4dBhp2BAcxYjyrIz8DaBc8NbZV0NQ4DtSsLFtgnJaw-tgrf6Uzov4Xxl_WZlm62BvKngcqWt6hrRattwo79lBRedUfbLNrqr4avRlfQX4ERx4-Vln4fg5f5uOX2MZs8PT9PJLOIkyduIlyXNc15RxoTK4hRnKZFKJLlQDJeEC5UmJcYVlpnKVJ6pcFacijhNc4YVqegQ3Oznbpz96KRvi1p7IY3hjbSdLyhOaBpTRsn_KMoCleCcBZTuUeGs906qYuN0zd22wKjYOVAEB4regaJ3IKiu-wVdWcvqoPl9eQDGe2CnXtvOhf_5P0f-AC0Dlbs</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>3073235189</pqid></control><display><type>article</type><title>A Platform for the Synthesis of Diverse Phosphonyl and Thiofunctionalized Sulfoxonium Ylides</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Zou, Wen-Xuan ; Hu, Qiong ; Shen, Dan-Ting ; Wu, Wen-Rong ; Wei, Jiaohang ; Yang, Zi-Feng ; Bao, Mei-Zhu ; Liu, Xiang ; Zhang, Shang-Shi</creator><creatorcontrib>Zou, Wen-Xuan ; Hu, Qiong ; Shen, Dan-Ting ; Wu, Wen-Rong ; Wei, Jiaohang ; Yang, Zi-Feng ; Bao, Mei-Zhu ; Liu, Xiang ; Zhang, Shang-Shi</creatorcontrib><description>A practical strategy for the construction of diverse phosphonyl and thiofunctionalized sulfoxonium ylides via controllable monofunctionalization of hybrid I(III)/S(VI) ylides is presented. This process allows efficient P–H insertion of I(III)/S(VI) ylides under Cu catalysis, enabling the synthesis of phosphonyl sulfoxonium ylides, whereas reaction with sulfur-containing reagents including AgSCF3, KSC­(S)­OR, and KSCN under mild conditions resulted in α-trifluoromethylthiolation, dithiocarbanation, and thiocyanation of sulfoxonium ylides accordingly. Of note, wide substrate compatibility (108 examples), excellent efficiency (up to 99% yield), gram-scale experiments, and various product derivatizations highlight the synthetic utility of this protocol.</description><identifier>ISSN: 1523-7060</identifier><identifier>ISSN: 1523-7052</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.4c02000</identifier><identifier>PMID: 38940397</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>catalytic activity ; derivatization ; utilities</subject><ispartof>Organic letters, 2024-07, Vol.26 (27), p.5811-5816</ispartof><rights>2024 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-a258t-abb388ad399cf7461762efc58cf91b2acf65b11d1e7f7f87f52346c466891f2d3</cites><orcidid>0000-0002-9247-1373 ; 0000-0001-6973-3809</orcidid></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/38940397$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zou, Wen-Xuan</creatorcontrib><creatorcontrib>Hu, Qiong</creatorcontrib><creatorcontrib>Shen, Dan-Ting</creatorcontrib><creatorcontrib>Wu, Wen-Rong</creatorcontrib><creatorcontrib>Wei, Jiaohang</creatorcontrib><creatorcontrib>Yang, Zi-Feng</creatorcontrib><creatorcontrib>Bao, Mei-Zhu</creatorcontrib><creatorcontrib>Liu, Xiang</creatorcontrib><creatorcontrib>Zhang, Shang-Shi</creatorcontrib><title>A Platform for the Synthesis of Diverse Phosphonyl and Thiofunctionalized Sulfoxonium Ylides</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>A practical strategy for the construction of diverse phosphonyl and thiofunctionalized sulfoxonium ylides via controllable monofunctionalization of hybrid I(III)/S(VI) ylides is presented. This process allows efficient P–H insertion of I(III)/S(VI) ylides under Cu catalysis, enabling the synthesis of phosphonyl sulfoxonium ylides, whereas reaction with sulfur-containing reagents including AgSCF3, KSC­(S)­OR, and KSCN under mild conditions resulted in α-trifluoromethylthiolation, dithiocarbanation, and thiocyanation of sulfoxonium ylides accordingly. Of note, wide substrate compatibility (108 examples), excellent efficiency (up to 99% yield), gram-scale experiments, and various product derivatizations highlight the synthetic utility of this protocol.</description><subject>catalytic activity</subject><subject>derivatization</subject><subject>utilities</subject><issn>1523-7060</issn><issn>1523-7052</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNqFkU1LAzEQhoMoVqu_QJAcvWybj_3KsdRPKFhoPQjCks0mNiW7qcmuWH-9KV171MvMMDzvDDMvAFcYjTAieMyFH1n3bmTbjmKBCELoCJzhhNAoQwk5PtQpGoBz79cI4dBhp2BAcxYjyrIz8DaBc8NbZV0NQ4DtSsLFtgnJaw-tgrf6Uzov4Xxl_WZlm62BvKngcqWt6hrRattwo79lBRedUfbLNrqr4avRlfQX4ERx4-Vln4fg5f5uOX2MZs8PT9PJLOIkyduIlyXNc15RxoTK4hRnKZFKJLlQDJeEC5UmJcYVlpnKVJ6pcFacijhNc4YVqegQ3Oznbpz96KRvi1p7IY3hjbSdLyhOaBpTRsn_KMoCleCcBZTuUeGs906qYuN0zd22wKjYOVAEB4regaJ3IKiu-wVdWcvqoPl9eQDGe2CnXtvOhf_5P0f-AC0Dlbs</recordid><startdate>20240712</startdate><enddate>20240712</enddate><creator>Zou, Wen-Xuan</creator><creator>Hu, Qiong</creator><creator>Shen, Dan-Ting</creator><creator>Wu, Wen-Rong</creator><creator>Wei, Jiaohang</creator><creator>Yang, Zi-Feng</creator><creator>Bao, Mei-Zhu</creator><creator>Liu, Xiang</creator><creator>Zhang, Shang-Shi</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7S9</scope><scope>L.6</scope><orcidid>https://orcid.org/0000-0002-9247-1373</orcidid><orcidid>https://orcid.org/0000-0001-6973-3809</orcidid></search><sort><creationdate>20240712</creationdate><title>A Platform for the Synthesis of Diverse Phosphonyl and Thiofunctionalized Sulfoxonium Ylides</title><author>Zou, Wen-Xuan ; Hu, Qiong ; Shen, Dan-Ting ; Wu, Wen-Rong ; Wei, Jiaohang ; Yang, Zi-Feng ; Bao, Mei-Zhu ; Liu, Xiang ; Zhang, Shang-Shi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a258t-abb388ad399cf7461762efc58cf91b2acf65b11d1e7f7f87f52346c466891f2d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>catalytic activity</topic><topic>derivatization</topic><topic>utilities</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zou, Wen-Xuan</creatorcontrib><creatorcontrib>Hu, Qiong</creatorcontrib><creatorcontrib>Shen, Dan-Ting</creatorcontrib><creatorcontrib>Wu, Wen-Rong</creatorcontrib><creatorcontrib>Wei, Jiaohang</creatorcontrib><creatorcontrib>Yang, Zi-Feng</creatorcontrib><creatorcontrib>Bao, Mei-Zhu</creatorcontrib><creatorcontrib>Liu, Xiang</creatorcontrib><creatorcontrib>Zhang, Shang-Shi</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zou, Wen-Xuan</au><au>Hu, Qiong</au><au>Shen, Dan-Ting</au><au>Wu, Wen-Rong</au><au>Wei, Jiaohang</au><au>Yang, Zi-Feng</au><au>Bao, Mei-Zhu</au><au>Liu, Xiang</au><au>Zhang, Shang-Shi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Platform for the Synthesis of Diverse Phosphonyl and Thiofunctionalized Sulfoxonium Ylides</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2024-07-12</date><risdate>2024</risdate><volume>26</volume><issue>27</issue><spage>5811</spage><epage>5816</epage><pages>5811-5816</pages><issn>1523-7060</issn><issn>1523-7052</issn><eissn>1523-7052</eissn><abstract>A practical strategy for the construction of diverse phosphonyl and thiofunctionalized sulfoxonium ylides via controllable monofunctionalization of hybrid I(III)/S(VI) ylides is presented. This process allows efficient P–H insertion of I(III)/S(VI) ylides under Cu catalysis, enabling the synthesis of phosphonyl sulfoxonium ylides, whereas reaction with sulfur-containing reagents including AgSCF3, KSC­(S)­OR, and KSCN under mild conditions resulted in α-trifluoromethylthiolation, dithiocarbanation, and thiocyanation of sulfoxonium ylides accordingly. Of note, wide substrate compatibility (108 examples), excellent efficiency (up to 99% yield), gram-scale experiments, and various product derivatizations highlight the synthetic utility of this protocol.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>38940397</pmid><doi>10.1021/acs.orglett.4c02000</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-9247-1373</orcidid><orcidid>https://orcid.org/0000-0001-6973-3809</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2024-07, Vol.26 (27), p.5811-5816
issn 1523-7060
1523-7052
1523-7052
language eng
recordid cdi_proquest_miscellaneous_3073235189
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects catalytic activity
derivatization
utilities
title A Platform for the Synthesis of Diverse Phosphonyl and Thiofunctionalized Sulfoxonium Ylides
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-20T01%3A00%3A00IST&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=A%20Platform%20for%20the%20Synthesis%20of%20Diverse%20Phosphonyl%20and%20Thiofunctionalized%20Sulfoxonium%20Ylides&rft.jtitle=Organic%20letters&rft.au=Zou,%20Wen-Xuan&rft.date=2024-07-12&rft.volume=26&rft.issue=27&rft.spage=5811&rft.epage=5816&rft.pages=5811-5816&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.4c02000&rft_dat=%3Cproquest_cross%3E3153643932%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a258t-abb388ad399cf7461762efc58cf91b2acf65b11d1e7f7f87f52346c466891f2d3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=3073235189&rft_id=info:pmid/38940397&rfr_iscdi=true