Synthesis of 2‑Acylbenzo[b]thiophenes via Cu-Catalyzed α‑C–H Functionalization of 2‑Halochalcones Using Xanthate

An efficient protocol is described for the synthesis of 2-acylbenzo­[b]­thiophenes from easily accessible 2-iodochalcones through α-C–H functionalization using Cu­(OAc)2 catalyst and xanthate as sulfur source. Less reactive 2-bromochalcones also yielded the corresponding 2-acylbenzothiophenes in goo...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2017-04, Vol.19 (7), p.1670-1673
Main Authors: Sangeetha, Subramani, Sekar, Govindasamy
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-a345t-eb23235d4fc274ac986a1df8f17d6064b91d6e6c3729adf7c393f78353cb5eef3
cites cdi_FETCH-LOGICAL-a345t-eb23235d4fc274ac986a1df8f17d6064b91d6e6c3729adf7c393f78353cb5eef3
container_end_page 1673
container_issue 7
container_start_page 1670
container_title Organic letters
container_volume 19
creator Sangeetha, Subramani
Sekar, Govindasamy
description An efficient protocol is described for the synthesis of 2-acylbenzo­[b]­thiophenes from easily accessible 2-iodochalcones through α-C–H functionalization using Cu­(OAc)2 catalyst and xanthate as sulfur source. Less reactive 2-bromochalcones also yielded the corresponding 2-acylbenzothiophenes in good yield. The reaction proceeds via in situ incorporation of sulfur followed by copper-catalyzed cyclization to generate 2-acylbenzothiophenes without external acyl source. The synthetic importance is showcased by synthesis of 1-(5-hydroxybenzothiophene-2-yl)­ethanone, which is a known pre-mRNA splicing modulator.
doi_str_mv 10.1021/acs.orglett.7b00462
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1881263095</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1881263095</sourcerecordid><originalsourceid>FETCH-LOGICAL-a345t-eb23235d4fc274ac986a1df8f17d6064b91d6e6c3729adf7c393f78353cb5eef3</originalsourceid><addsrcrecordid>eNp9kEtKxEAQhhtRfJ9AkCzdZOxH0kmWEhxHEFyoIIiESqfaifSkx3RHyKy8gngSL-IhPIkZZnTpqori-_-Cj5AjRkeMcnYKyo1s-2TQ-1FSUhpJvkF2WcxFmNCYb_7tku6QPeeeKWXDJdsmOzwVQkQy2yX9Td_4KbraBVYH_Pvt_Uz1psRmYR_KRz-t7XyKDbrgtYYg78IcPJh-gVXw9TnA-ffbxyQYd43ytW3A1AtYLr9dEzBWTcEou6y4c3XzFNzD8BA8HpAtDcbh4Xruk7vx-W0-Ca-uLy7zs6sQRBT7EEsuuIirSCueRKCyVAKrdKpZUkkqozJjlUSpRMIzqHSiRCZ0kopYqDJG1GKfnKx656196dD5YlY7hcZAg7ZzBUtTxqWgWTygYoWq1jrXoi7mbT2Dti8YLZbOi8F5sXZerJ0PqeP1g66cYfWX-ZU8AKcrYJl-tl07iHL_Vv4AxWGWyQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1881263095</pqid></control><display><type>article</type><title>Synthesis of 2‑Acylbenzo[b]thiophenes via Cu-Catalyzed α‑C–H Functionalization of 2‑Halochalcones Using Xanthate</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Sangeetha, Subramani ; Sekar, Govindasamy</creator><creatorcontrib>Sangeetha, Subramani ; Sekar, Govindasamy</creatorcontrib><description>An efficient protocol is described for the synthesis of 2-acylbenzo­[b]­thiophenes from easily accessible 2-iodochalcones through α-C–H functionalization using Cu­(OAc)2 catalyst and xanthate as sulfur source. Less reactive 2-bromochalcones also yielded the corresponding 2-acylbenzothiophenes in good yield. The reaction proceeds via in situ incorporation of sulfur followed by copper-catalyzed cyclization to generate 2-acylbenzothiophenes without external acyl source. The synthetic importance is showcased by synthesis of 1-(5-hydroxybenzothiophene-2-yl)­ethanone, which is a known pre-mRNA splicing modulator.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.7b00462</identifier><identifier>PMID: 28333469</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2017-04, Vol.19 (7), p.1670-1673</ispartof><rights>Copyright © 2017 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a345t-eb23235d4fc274ac986a1df8f17d6064b91d6e6c3729adf7c393f78353cb5eef3</citedby><cites>FETCH-LOGICAL-a345t-eb23235d4fc274ac986a1df8f17d6064b91d6e6c3729adf7c393f78353cb5eef3</cites><orcidid>0000-0003-2294-0485</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28333469$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Sangeetha, Subramani</creatorcontrib><creatorcontrib>Sekar, Govindasamy</creatorcontrib><title>Synthesis of 2‑Acylbenzo[b]thiophenes via Cu-Catalyzed α‑C–H Functionalization of 2‑Halochalcones Using Xanthate</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>An efficient protocol is described for the synthesis of 2-acylbenzo­[b]­thiophenes from easily accessible 2-iodochalcones through α-C–H functionalization using Cu­(OAc)2 catalyst and xanthate as sulfur source. Less reactive 2-bromochalcones also yielded the corresponding 2-acylbenzothiophenes in good yield. The reaction proceeds via in situ incorporation of sulfur followed by copper-catalyzed cyclization to generate 2-acylbenzothiophenes without external acyl source. The synthetic importance is showcased by synthesis of 1-(5-hydroxybenzothiophene-2-yl)­ethanone, which is a known pre-mRNA splicing modulator.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNp9kEtKxEAQhhtRfJ9AkCzdZOxH0kmWEhxHEFyoIIiESqfaifSkx3RHyKy8gngSL-IhPIkZZnTpqori-_-Cj5AjRkeMcnYKyo1s-2TQ-1FSUhpJvkF2WcxFmNCYb_7tku6QPeeeKWXDJdsmOzwVQkQy2yX9Td_4KbraBVYH_Pvt_Uz1psRmYR_KRz-t7XyKDbrgtYYg78IcPJh-gVXw9TnA-ffbxyQYd43ytW3A1AtYLr9dEzBWTcEou6y4c3XzFNzD8BA8HpAtDcbh4Xruk7vx-W0-Ca-uLy7zs6sQRBT7EEsuuIirSCueRKCyVAKrdKpZUkkqozJjlUSpRMIzqHSiRCZ0kopYqDJG1GKfnKx656196dD5YlY7hcZAg7ZzBUtTxqWgWTygYoWq1jrXoi7mbT2Dti8YLZbOi8F5sXZerJ0PqeP1g66cYfWX-ZU8AKcrYJl-tl07iHL_Vv4AxWGWyQ</recordid><startdate>20170407</startdate><enddate>20170407</enddate><creator>Sangeetha, Subramani</creator><creator>Sekar, Govindasamy</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-2294-0485</orcidid></search><sort><creationdate>20170407</creationdate><title>Synthesis of 2‑Acylbenzo[b]thiophenes via Cu-Catalyzed α‑C–H Functionalization of 2‑Halochalcones Using Xanthate</title><author>Sangeetha, Subramani ; Sekar, Govindasamy</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a345t-eb23235d4fc274ac986a1df8f17d6064b91d6e6c3729adf7c393f78353cb5eef3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sangeetha, Subramani</creatorcontrib><creatorcontrib>Sekar, Govindasamy</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sangeetha, Subramani</au><au>Sekar, Govindasamy</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of 2‑Acylbenzo[b]thiophenes via Cu-Catalyzed α‑C–H Functionalization of 2‑Halochalcones Using Xanthate</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2017-04-07</date><risdate>2017</risdate><volume>19</volume><issue>7</issue><spage>1670</spage><epage>1673</epage><pages>1670-1673</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>An efficient protocol is described for the synthesis of 2-acylbenzo­[b]­thiophenes from easily accessible 2-iodochalcones through α-C–H functionalization using Cu­(OAc)2 catalyst and xanthate as sulfur source. Less reactive 2-bromochalcones also yielded the corresponding 2-acylbenzothiophenes in good yield. The reaction proceeds via in situ incorporation of sulfur followed by copper-catalyzed cyclization to generate 2-acylbenzothiophenes without external acyl source. The synthetic importance is showcased by synthesis of 1-(5-hydroxybenzothiophene-2-yl)­ethanone, which is a known pre-mRNA splicing modulator.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>28333469</pmid><doi>10.1021/acs.orglett.7b00462</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0003-2294-0485</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2017-04, Vol.19 (7), p.1670-1673
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_1881263095
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
title Synthesis of 2‑Acylbenzo[b]thiophenes via Cu-Catalyzed α‑C–H Functionalization of 2‑Halochalcones Using Xanthate
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-05T06%3A56%3A19IST&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=Synthesis%20of%202%E2%80%91Acylbenzo%5Bb%5Dthiophenes%20via%20Cu-Catalyzed%20%CE%B1%E2%80%91C%E2%80%93H%20Functionalization%20of%202%E2%80%91Halochalcones%20Using%20Xanthate&rft.jtitle=Organic%20letters&rft.au=Sangeetha,%20Subramani&rft.date=2017-04-07&rft.volume=19&rft.issue=7&rft.spage=1670&rft.epage=1673&rft.pages=1670-1673&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.7b00462&rft_dat=%3Cproquest_cross%3E1881263095%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a345t-eb23235d4fc274ac986a1df8f17d6064b91d6e6c3729adf7c393f78353cb5eef3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1881263095&rft_id=info:pmid/28333469&rfr_iscdi=true