Palladium-Catalyzed Direct C–H Arylation of 3‑(Methylsulfinyl)thiophenes

A palladium-catalyzed direct arylation of (3-thiophene)­S­(O)­Me derivatives has been developed. This protocol is effective for the selective synthesis of 2-arylated and 2,5-diarylated sulfinylthiophene derivatives with as low as 0.5 mol % catalyst loading. Various functional groups are well tolerat...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2018-05, Vol.20 (9), p.2522-2525
Hauptverfasser: Jiang, Hui, Bellomo, Ana, Zhang, Mengnan, Carroll, Patrick J, Manor, Brian C, Jia, Tiezheng, Walsh, Patrick J
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 2525
container_issue 9
container_start_page 2522
container_title Organic letters
container_volume 20
creator Jiang, Hui
Bellomo, Ana
Zhang, Mengnan
Carroll, Patrick J
Manor, Brian C
Jia, Tiezheng
Walsh, Patrick J
description A palladium-catalyzed direct arylation of (3-thiophene)­S­(O)­Me derivatives has been developed. This protocol is effective for the selective synthesis of 2-arylated and 2,5-diarylated sulfinylthiophene derivatives with as low as 0.5 mol % catalyst loading. Various functional groups are well tolerated. A method to install two different aryl groups on 3-(methylsulfinyl)­thiophenes is also introduced.
doi_str_mv 10.1021/acs.orglett.8b00599
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2026416050</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2026416050</sourcerecordid><originalsourceid>FETCH-LOGICAL-a345t-f7bb3b4894c1aa72468deacbe0eba1fd80b6d520146cbd3fe11b2817b9151ae93</originalsourceid><addsrcrecordid>eNp9kE1OwzAQhS0EoqVwAiSUZVmktZ1fL6vyU6QiWMDaspMJTeXExXYWYdUrIG7Yk5CqoUtWMxq990bvQ-ia4AnBlExFZifafChwbpJKjCPGTtCQRDTwExzR0-Me4wG6sHaNMeku7BwNKIsjRlk4RMtXoZTIy6by58IJ1X5B7t2VBjLnzXfbn4U3M60SrtS1pwsv2G2_x8_gVq2yjSrKulW3blXqzQpqsJforBDKwlU_R-j94f5tvvCXL49P89nSF0EYOb9IpAxkmLIwI0IkNIzTHEQmAYMUpMhTLOM8opiEcSbzoABCJE1JIhmJiAAWjND4kLsx-rMB63hV2gy6IjXoxnKKaRySGEe4kwYHaWa0tQYKvjFlJUzLCeZ7jLzDyHuMvMfYuW76B42sID96_rh1gulBsHevdWPqru-_kb96ZoPp</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2026416050</pqid></control><display><type>article</type><title>Palladium-Catalyzed Direct C–H Arylation of 3‑(Methylsulfinyl)thiophenes</title><source>American Chemical Society Journals</source><creator>Jiang, Hui ; Bellomo, Ana ; Zhang, Mengnan ; Carroll, Patrick J ; Manor, Brian C ; Jia, Tiezheng ; Walsh, Patrick J</creator><creatorcontrib>Jiang, Hui ; Bellomo, Ana ; Zhang, Mengnan ; Carroll, Patrick J ; Manor, Brian C ; Jia, Tiezheng ; Walsh, Patrick J</creatorcontrib><description>A palladium-catalyzed direct arylation of (3-thiophene)­S­(O)­Me derivatives has been developed. This protocol is effective for the selective synthesis of 2-arylated and 2,5-diarylated sulfinylthiophene derivatives with as low as 0.5 mol % catalyst loading. Various functional groups are well tolerated. A method to install two different aryl groups on 3-(methylsulfinyl)­thiophenes is also introduced.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.8b00599</identifier><identifier>PMID: 29659294</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2018-05, Vol.20 (9), p.2522-2525</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a345t-f7bb3b4894c1aa72468deacbe0eba1fd80b6d520146cbd3fe11b2817b9151ae93</citedby><cites>FETCH-LOGICAL-a345t-f7bb3b4894c1aa72468deacbe0eba1fd80b6d520146cbd3fe11b2817b9151ae93</cites><orcidid>0000-0001-6431-3004 ; 0000-0001-8392-4150</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.orglett.8b00599$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.orglett.8b00599$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29659294$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Jiang, Hui</creatorcontrib><creatorcontrib>Bellomo, Ana</creatorcontrib><creatorcontrib>Zhang, Mengnan</creatorcontrib><creatorcontrib>Carroll, Patrick J</creatorcontrib><creatorcontrib>Manor, Brian C</creatorcontrib><creatorcontrib>Jia, Tiezheng</creatorcontrib><creatorcontrib>Walsh, Patrick J</creatorcontrib><title>Palladium-Catalyzed Direct C–H Arylation of 3‑(Methylsulfinyl)thiophenes</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>A palladium-catalyzed direct arylation of (3-thiophene)­S­(O)­Me derivatives has been developed. This protocol is effective for the selective synthesis of 2-arylated and 2,5-diarylated sulfinylthiophene derivatives with as low as 0.5 mol % catalyst loading. Various functional groups are well tolerated. A method to install two different aryl groups on 3-(methylsulfinyl)­thiophenes is also introduced.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNp9kE1OwzAQhS0EoqVwAiSUZVmktZ1fL6vyU6QiWMDaspMJTeXExXYWYdUrIG7Yk5CqoUtWMxq990bvQ-ia4AnBlExFZifafChwbpJKjCPGTtCQRDTwExzR0-Me4wG6sHaNMeku7BwNKIsjRlk4RMtXoZTIy6by58IJ1X5B7t2VBjLnzXfbn4U3M60SrtS1pwsv2G2_x8_gVq2yjSrKulW3blXqzQpqsJforBDKwlU_R-j94f5tvvCXL49P89nSF0EYOb9IpAxkmLIwI0IkNIzTHEQmAYMUpMhTLOM8opiEcSbzoABCJE1JIhmJiAAWjND4kLsx-rMB63hV2gy6IjXoxnKKaRySGEe4kwYHaWa0tQYKvjFlJUzLCeZ7jLzDyHuMvMfYuW76B42sID96_rh1gulBsHevdWPqru-_kb96ZoPp</recordid><startdate>20180504</startdate><enddate>20180504</enddate><creator>Jiang, Hui</creator><creator>Bellomo, Ana</creator><creator>Zhang, Mengnan</creator><creator>Carroll, Patrick J</creator><creator>Manor, Brian C</creator><creator>Jia, Tiezheng</creator><creator>Walsh, Patrick J</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-6431-3004</orcidid><orcidid>https://orcid.org/0000-0001-8392-4150</orcidid></search><sort><creationdate>20180504</creationdate><title>Palladium-Catalyzed Direct C–H Arylation of 3‑(Methylsulfinyl)thiophenes</title><author>Jiang, Hui ; Bellomo, Ana ; Zhang, Mengnan ; Carroll, Patrick J ; Manor, Brian C ; Jia, Tiezheng ; Walsh, Patrick J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a345t-f7bb3b4894c1aa72468deacbe0eba1fd80b6d520146cbd3fe11b2817b9151ae93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jiang, Hui</creatorcontrib><creatorcontrib>Bellomo, Ana</creatorcontrib><creatorcontrib>Zhang, Mengnan</creatorcontrib><creatorcontrib>Carroll, Patrick J</creatorcontrib><creatorcontrib>Manor, Brian C</creatorcontrib><creatorcontrib>Jia, Tiezheng</creatorcontrib><creatorcontrib>Walsh, Patrick J</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>Jiang, Hui</au><au>Bellomo, Ana</au><au>Zhang, Mengnan</au><au>Carroll, Patrick J</au><au>Manor, Brian C</au><au>Jia, Tiezheng</au><au>Walsh, Patrick J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Palladium-Catalyzed Direct C–H Arylation of 3‑(Methylsulfinyl)thiophenes</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2018-05-04</date><risdate>2018</risdate><volume>20</volume><issue>9</issue><spage>2522</spage><epage>2525</epage><pages>2522-2525</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>A palladium-catalyzed direct arylation of (3-thiophene)­S­(O)­Me derivatives has been developed. This protocol is effective for the selective synthesis of 2-arylated and 2,5-diarylated sulfinylthiophene derivatives with as low as 0.5 mol % catalyst loading. Various functional groups are well tolerated. A method to install two different aryl groups on 3-(methylsulfinyl)­thiophenes is also introduced.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>29659294</pmid><doi>10.1021/acs.orglett.8b00599</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0001-6431-3004</orcidid><orcidid>https://orcid.org/0000-0001-8392-4150</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2018-05, Vol.20 (9), p.2522-2525
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_2026416050
source American Chemical Society Journals
title Palladium-Catalyzed Direct C–H Arylation of 3‑(Methylsulfinyl)thiophenes
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-23T06%3A17%3A49IST&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=Palladium-Catalyzed%20Direct%20C%E2%80%93H%20Arylation%20of%203%E2%80%91(Methylsulfinyl)thiophenes&rft.jtitle=Organic%20letters&rft.au=Jiang,%20Hui&rft.date=2018-05-04&rft.volume=20&rft.issue=9&rft.spage=2522&rft.epage=2525&rft.pages=2522-2525&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.8b00599&rft_dat=%3Cproquest_cross%3E2026416050%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=2026416050&rft_id=info:pmid/29659294&rfr_iscdi=true