Palladium-Catalyzed Decarbonylative Sonogashira Coupling of Terminal Alkynes with Carboxylic Acids

A direct decarbonylative Sonogashira coupling of terminal alkynes with carboxylic acids was achieved through palladium catalysis. This reaction did not use overstoichiometric oxidants, thus overcoming the homocoupling issue of terminal alkynes. Under the reaction conditions, a wide range of carboxyl...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2021-05, Vol.23 (9), p.3304-3309
Hauptverfasser: Li, Xinyi, Liu, Long, Huang, Tianzeng, Tang, Zhi, Li, Chunya, Li, Wenhui, Zhang, Tao, Li, Zhaohui, Chen, Tieqiao
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 3309
container_issue 9
container_start_page 3304
container_title Organic letters
container_volume 23
creator Li, Xinyi
Liu, Long
Huang, Tianzeng
Tang, Zhi
Li, Chunya
Li, Wenhui
Zhang, Tao
Li, Zhaohui
Chen, Tieqiao
description A direct decarbonylative Sonogashira coupling of terminal alkynes with carboxylic acids was achieved through palladium catalysis. This reaction did not use overstoichiometric oxidants, thus overcoming the homocoupling issue of terminal alkynes. Under the reaction conditions, a wide range of carboxylic acids including those bioactive ones could couple readily with various terminal alkynes, thus providing a relative general method for preparing internal alkynes.
doi_str_mv 10.1021/acs.orglett.1c00768
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2516221890</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2516221890</sourcerecordid><originalsourceid>FETCH-LOGICAL-a345t-82ec7c8a12d0c831252791122e85e73e03e291a6e82bd3827c125b6987bc02a23</originalsourceid><addsrcrecordid>eNp9kE1LxDAQhoMofv8CQXL00t1kYpv0uNRPEBTUc0nT2TWaNmvSqvXX22VXj55mGJ53hnkIOeFswhnwqTZx4sPCYddNuGFMZmqL7PMURCJZCtt_fcb2yEGMr4zxcZLvkj0hlFSQyX1SPWjndG37Jil0p93wjTW9QKND5dvB6c5-IH30rV_o-GKDpoXvl862C-rn9AlDY1vt6My9DS1G-mm7F1qssl-Ds4bOjK3jEdmZaxfxeFMPyfPV5VNxk9zdX98Ws7tEi_O0SxSgkUZpDjUzSnBIQeacA6BKUQpkAiHnOkMFVS0USDMiVZYrWRkGGsQhOVvvXQb_3mPsysZGg-N7Lfo-lpDyDICrnI2oWKMm-BgDzstlsI0OQ8lZuZJbjnLLjdxyI3dMnW4O9FWD9V_m1-YITNfAKv3q-zC6if-u_AHifokU</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2516221890</pqid></control><display><type>article</type><title>Palladium-Catalyzed Decarbonylative Sonogashira Coupling of Terminal Alkynes with Carboxylic Acids</title><source>American Chemical Society Journals</source><creator>Li, Xinyi ; Liu, Long ; Huang, Tianzeng ; Tang, Zhi ; Li, Chunya ; Li, Wenhui ; Zhang, Tao ; Li, Zhaohui ; Chen, Tieqiao</creator><creatorcontrib>Li, Xinyi ; Liu, Long ; Huang, Tianzeng ; Tang, Zhi ; Li, Chunya ; Li, Wenhui ; Zhang, Tao ; Li, Zhaohui ; Chen, Tieqiao</creatorcontrib><description>A direct decarbonylative Sonogashira coupling of terminal alkynes with carboxylic acids was achieved through palladium catalysis. This reaction did not use overstoichiometric oxidants, thus overcoming the homocoupling issue of terminal alkynes. Under the reaction conditions, a wide range of carboxylic acids including those bioactive ones could couple readily with various terminal alkynes, thus providing a relative general method for preparing internal alkynes.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.1c00768</identifier><identifier>PMID: 33878267</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2021-05, Vol.23 (9), p.3304-3309</ispartof><rights>2021 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a345t-82ec7c8a12d0c831252791122e85e73e03e291a6e82bd3827c125b6987bc02a23</citedby><cites>FETCH-LOGICAL-a345t-82ec7c8a12d0c831252791122e85e73e03e291a6e82bd3827c125b6987bc02a23</cites><orcidid>0000-0002-6472-5057 ; 0000-0002-9787-9538</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.1c00768$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.orglett.1c00768$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33878267$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Li, Xinyi</creatorcontrib><creatorcontrib>Liu, Long</creatorcontrib><creatorcontrib>Huang, Tianzeng</creatorcontrib><creatorcontrib>Tang, Zhi</creatorcontrib><creatorcontrib>Li, Chunya</creatorcontrib><creatorcontrib>Li, Wenhui</creatorcontrib><creatorcontrib>Zhang, Tao</creatorcontrib><creatorcontrib>Li, Zhaohui</creatorcontrib><creatorcontrib>Chen, Tieqiao</creatorcontrib><title>Palladium-Catalyzed Decarbonylative Sonogashira Coupling of Terminal Alkynes with Carboxylic Acids</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>A direct decarbonylative Sonogashira coupling of terminal alkynes with carboxylic acids was achieved through palladium catalysis. This reaction did not use overstoichiometric oxidants, thus overcoming the homocoupling issue of terminal alkynes. Under the reaction conditions, a wide range of carboxylic acids including those bioactive ones could couple readily with various terminal alkynes, thus providing a relative general method for preparing internal alkynes.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNp9kE1LxDAQhoMofv8CQXL00t1kYpv0uNRPEBTUc0nT2TWaNmvSqvXX22VXj55mGJ53hnkIOeFswhnwqTZx4sPCYddNuGFMZmqL7PMURCJZCtt_fcb2yEGMr4zxcZLvkj0hlFSQyX1SPWjndG37Jil0p93wjTW9QKND5dvB6c5-IH30rV_o-GKDpoXvl862C-rn9AlDY1vt6My9DS1G-mm7F1qssl-Ds4bOjK3jEdmZaxfxeFMPyfPV5VNxk9zdX98Ws7tEi_O0SxSgkUZpDjUzSnBIQeacA6BKUQpkAiHnOkMFVS0USDMiVZYrWRkGGsQhOVvvXQb_3mPsysZGg-N7Lfo-lpDyDICrnI2oWKMm-BgDzstlsI0OQ8lZuZJbjnLLjdxyI3dMnW4O9FWD9V_m1-YITNfAKv3q-zC6if-u_AHifokU</recordid><startdate>20210507</startdate><enddate>20210507</enddate><creator>Li, Xinyi</creator><creator>Liu, Long</creator><creator>Huang, Tianzeng</creator><creator>Tang, Zhi</creator><creator>Li, Chunya</creator><creator>Li, Wenhui</creator><creator>Zhang, Tao</creator><creator>Li, Zhaohui</creator><creator>Chen, Tieqiao</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-6472-5057</orcidid><orcidid>https://orcid.org/0000-0002-9787-9538</orcidid></search><sort><creationdate>20210507</creationdate><title>Palladium-Catalyzed Decarbonylative Sonogashira Coupling of Terminal Alkynes with Carboxylic Acids</title><author>Li, Xinyi ; Liu, Long ; Huang, Tianzeng ; Tang, Zhi ; Li, Chunya ; Li, Wenhui ; Zhang, Tao ; Li, Zhaohui ; Chen, Tieqiao</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a345t-82ec7c8a12d0c831252791122e85e73e03e291a6e82bd3827c125b6987bc02a23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Xinyi</creatorcontrib><creatorcontrib>Liu, Long</creatorcontrib><creatorcontrib>Huang, Tianzeng</creatorcontrib><creatorcontrib>Tang, Zhi</creatorcontrib><creatorcontrib>Li, Chunya</creatorcontrib><creatorcontrib>Li, Wenhui</creatorcontrib><creatorcontrib>Zhang, Tao</creatorcontrib><creatorcontrib>Li, Zhaohui</creatorcontrib><creatorcontrib>Chen, Tieqiao</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>Li, Xinyi</au><au>Liu, Long</au><au>Huang, Tianzeng</au><au>Tang, Zhi</au><au>Li, Chunya</au><au>Li, Wenhui</au><au>Zhang, Tao</au><au>Li, Zhaohui</au><au>Chen, Tieqiao</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Palladium-Catalyzed Decarbonylative Sonogashira Coupling of Terminal Alkynes with Carboxylic Acids</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2021-05-07</date><risdate>2021</risdate><volume>23</volume><issue>9</issue><spage>3304</spage><epage>3309</epage><pages>3304-3309</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>A direct decarbonylative Sonogashira coupling of terminal alkynes with carboxylic acids was achieved through palladium catalysis. This reaction did not use overstoichiometric oxidants, thus overcoming the homocoupling issue of terminal alkynes. Under the reaction conditions, a wide range of carboxylic acids including those bioactive ones could couple readily with various terminal alkynes, thus providing a relative general method for preparing internal alkynes.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>33878267</pmid><doi>10.1021/acs.orglett.1c00768</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-6472-5057</orcidid><orcidid>https://orcid.org/0000-0002-9787-9538</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2021-05, Vol.23 (9), p.3304-3309
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_2516221890
source American Chemical Society Journals
title Palladium-Catalyzed Decarbonylative Sonogashira Coupling of Terminal Alkynes with Carboxylic Acids
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-29T02%3A34%3A04IST&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%20Decarbonylative%20Sonogashira%20Coupling%20of%20Terminal%20Alkynes%20with%20Carboxylic%20Acids&rft.jtitle=Organic%20letters&rft.au=Li,%20Xinyi&rft.date=2021-05-07&rft.volume=23&rft.issue=9&rft.spage=3304&rft.epage=3309&rft.pages=3304-3309&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.1c00768&rft_dat=%3Cproquest_cross%3E2516221890%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=2516221890&rft_id=info:pmid/33878267&rfr_iscdi=true