Site-Selective Electrophilic Trifluoromethylthiolation for the Synthesis of C5- or C7-SCF3-Substituted Indolines

We report herein an efficient and site-selective electrophilic trifluoromethylthiolation of indolines. In the absence of any catalyst or additive, C5-selective trifluoromethylthiolation could proceed at room temperature. With palladium used as the catalyst, the selectivity was reversed completely, g...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Organic letters 2024-12
Hauptverfasser:	Wang, Xiaolong, Fu, Yan, Guo, Zhenshan, Lin, Aijun, Jia, Qingzhong, Han, Chunhua
Format:	Artikel
Sprache:	eng
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

container_end_page
container_issue
container_start_page
container_title	Organic letters
container_volume
creator	Wang, Xiaolong Fu, Yan Guo, Zhenshan Lin, Aijun Jia, Qingzhong Han, Chunhua
description	We report herein an efficient and site-selective electrophilic trifluoromethylthiolation of indolines. In the absence of any catalyst or additive, C5-selective trifluoromethylthiolation could proceed at room temperature. With palladium used as the catalyst, the selectivity was reversed completely, giving C7-selecive trifluoromethylthiolated products. This reaction features good functional group tolerance, simple operation, mild conditions, and scale-up application. The potential utilities of the products were shown by further transformations.We report herein an efficient and site-selective electrophilic trifluoromethylthiolation of indolines. In the absence of any catalyst or additive, C5-selective trifluoromethylthiolation could proceed at room temperature. With palladium used as the catalyst, the selectivity was reversed completely, giving C7-selecive trifluoromethylthiolated products. This reaction features good functional group tolerance, simple operation, mild conditions, and scale-up application. The potential utilities of the products were shown by further transformations.
doi_str_mv	10.1021/acs.orglett.4c04500
format	Article
fullrecord	<record><control><sourceid>proquest</sourceid><recordid>TN_cdi_proquest_miscellaneous_3148496056</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3148496056</sourcerecordid><originalsourceid>FETCH-proquest_miscellaneous_31484960563</originalsourceid><addsrcrecordid>eNqVij1PwzAQQC1EJcrHL2DxyOJgJ3FL56gVzO5ehfTSHHJ9wXdB6r8nSAysTO_p6Sn16GzhbOme244LyqcIIkXd2dpbe6WWzpeVWVtfXv_xG3XL_GGtm8tmqcaAAiZAhE7wC_T2RzKNA0bs9D5jHyfKdAYZLlEGpNgKUtI9ZS0D6HBJMxhZU68bb_Tcm7UJza4yYXpnQZkEjvotHSliAr5Xi76NDA-_vFNPu-2-eTVjps8JWA5n5A5ibBPQxIfK1S_1ZmX9qvrH-g1nkVey</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>3148496056</pqid></control><display><type>article</type><title>Site-Selective Electrophilic Trifluoromethylthiolation for the Synthesis of C5- or C7-SCF3-Substituted Indolines</title><source>ACS Publications</source><creator>Wang, Xiaolong ; Fu, Yan ; Guo, Zhenshan ; Lin, Aijun ; Jia, Qingzhong ; Han, Chunhua</creator><creatorcontrib>Wang, Xiaolong ; Fu, Yan ; Guo, Zhenshan ; Lin, Aijun ; Jia, Qingzhong ; Han, Chunhua</creatorcontrib><description>We report herein an efficient and site-selective electrophilic trifluoromethylthiolation of indolines. In the absence of any catalyst or additive, C5-selective trifluoromethylthiolation could proceed at room temperature. With palladium used as the catalyst, the selectivity was reversed completely, giving C7-selecive trifluoromethylthiolated products. This reaction features good functional group tolerance, simple operation, mild conditions, and scale-up application. The potential utilities of the products were shown by further transformations.We report herein an efficient and site-selective electrophilic trifluoromethylthiolation of indolines. In the absence of any catalyst or additive, C5-selective trifluoromethylthiolation could proceed at room temperature. With palladium used as the catalyst, the selectivity was reversed completely, giving C7-selecive trifluoromethylthiolated products. This reaction features good functional group tolerance, simple operation, mild conditions, and scale-up application. The potential utilities of the products were shown by further transformations.</description><identifier>ISSN: 1523-7052</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.4c04500</identifier><language>eng</language><ispartof>Organic letters, 2024-12</ispartof><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>314,780,784,27922,27923</link.rule.ids></links><search><creatorcontrib>Wang, Xiaolong</creatorcontrib><creatorcontrib>Fu, Yan</creatorcontrib><creatorcontrib>Guo, Zhenshan</creatorcontrib><creatorcontrib>Lin, Aijun</creatorcontrib><creatorcontrib>Jia, Qingzhong</creatorcontrib><creatorcontrib>Han, Chunhua</creatorcontrib><title>Site-Selective Electrophilic Trifluoromethylthiolation for the Synthesis of C5- or C7-SCF3-Substituted Indolines</title><title>Organic letters</title><description>We report herein an efficient and site-selective electrophilic trifluoromethylthiolation of indolines. In the absence of any catalyst or additive, C5-selective trifluoromethylthiolation could proceed at room temperature. With palladium used as the catalyst, the selectivity was reversed completely, giving C7-selecive trifluoromethylthiolated products. This reaction features good functional group tolerance, simple operation, mild conditions, and scale-up application. The potential utilities of the products were shown by further transformations.We report herein an efficient and site-selective electrophilic trifluoromethylthiolation of indolines. In the absence of any catalyst or additive, C5-selective trifluoromethylthiolation could proceed at room temperature. With palladium used as the catalyst, the selectivity was reversed completely, giving C7-selecive trifluoromethylthiolated products. This reaction features good functional group tolerance, simple operation, mild conditions, and scale-up application. The potential utilities of the products were shown by further transformations.</description><issn>1523-7052</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNqVij1PwzAQQC1EJcrHL2DxyOJgJ3FL56gVzO5ehfTSHHJ9wXdB6r8nSAysTO_p6Sn16GzhbOme244LyqcIIkXd2dpbe6WWzpeVWVtfXv_xG3XL_GGtm8tmqcaAAiZAhE7wC_T2RzKNA0bs9D5jHyfKdAYZLlEGpNgKUtI9ZS0D6HBJMxhZU68bb_Tcm7UJza4yYXpnQZkEjvotHSliAr5Xi76NDA-_vFNPu-2-eTVjps8JWA5n5A5ibBPQxIfK1S_1ZmX9qvrH-g1nkVey</recordid><startdate>20241223</startdate><enddate>20241223</enddate><creator>Wang, Xiaolong</creator><creator>Fu, Yan</creator><creator>Guo, Zhenshan</creator><creator>Lin, Aijun</creator><creator>Jia, Qingzhong</creator><creator>Han, Chunhua</creator><scope>7X8</scope></search><sort><creationdate>20241223</creationdate><title>Site-Selective Electrophilic Trifluoromethylthiolation for the Synthesis of C5- or C7-SCF3-Substituted Indolines</title><author>Wang, Xiaolong ; Fu, Yan ; Guo, Zhenshan ; Lin, Aijun ; Jia, Qingzhong ; Han, Chunhua</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-proquest_miscellaneous_31484960563</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Xiaolong</creatorcontrib><creatorcontrib>Fu, Yan</creatorcontrib><creatorcontrib>Guo, Zhenshan</creatorcontrib><creatorcontrib>Lin, Aijun</creatorcontrib><creatorcontrib>Jia, Qingzhong</creatorcontrib><creatorcontrib>Han, Chunhua</creatorcontrib><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Xiaolong</au><au>Fu, Yan</au><au>Guo, Zhenshan</au><au>Lin, Aijun</au><au>Jia, Qingzhong</au><au>Han, Chunhua</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Site-Selective Electrophilic Trifluoromethylthiolation for the Synthesis of C5- or C7-SCF3-Substituted Indolines</atitle><jtitle>Organic letters</jtitle><date>2024-12-23</date><risdate>2024</risdate><issn>1523-7052</issn><eissn>1523-7052</eissn><abstract>We report herein an efficient and site-selective electrophilic trifluoromethylthiolation of indolines. In the absence of any catalyst or additive, C5-selective trifluoromethylthiolation could proceed at room temperature. With palladium used as the catalyst, the selectivity was reversed completely, giving C7-selecive trifluoromethylthiolated products. This reaction features good functional group tolerance, simple operation, mild conditions, and scale-up application. The potential utilities of the products were shown by further transformations.We report herein an efficient and site-selective electrophilic trifluoromethylthiolation of indolines. In the absence of any catalyst or additive, C5-selective trifluoromethylthiolation could proceed at room temperature. With palladium used as the catalyst, the selectivity was reversed completely, giving C7-selecive trifluoromethylthiolated products. This reaction features good functional group tolerance, simple operation, mild conditions, and scale-up application. The potential utilities of the products were shown by further transformations.</abstract><doi>10.1021/acs.orglett.4c04500</doi></addata></record>
fulltext	fulltext
identifier	ISSN: 1523-7052
ispartof	Organic letters, 2024-12
issn	1523-7052 1523-7052
language	eng
recordid	cdi_proquest_miscellaneous_3148496056
source	ACS Publications
title	Site-Selective Electrophilic Trifluoromethylthiolation for the Synthesis of C5- or C7-SCF3-Substituted Indolines
url	https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-09T18%3A25%3A09IST&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=Site-Selective%20Electrophilic%20Trifluoromethylthiolation%20for%20the%20Synthesis%20of%20C5-%20or%20C7-SCF3-Substituted%20Indolines&rft.jtitle=Organic%20letters&rft.au=Wang,%20Xiaolong&rft.date=2024-12-23&rft.issn=1523-7052&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.4c04500&rft_dat=%3Cproquest%3E3148496056%3C/proquest%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=3148496056&rft_id=info:pmid/&rfr_iscdi=true