Deoxygenative trifluoromethylthiolation of carboxylic acids

Deoxygenative trifluoromethylthiolation of carboxylic acids

Here we describe a deoxygenative trifluoromethylthiolation method that yields trifluoromethyl thioesters from readily available carboxylic acids. The method is built upon an umpolung strategy where triphenylphosphine is used to first activate an electrophilic trifluoromethylthiolating reagent and th...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Chemical science (Cambridge) 2019-11, Vol.1 (41), p.9555-9559
Hauptverfasser: Mao, Runze, Bera, Srikrishna, Cheseaux, Alexis, Hu, Xile
Format: Artikel
Sprache:eng
Schlagworte:
Carboxylic acids
Chemistry
Deoxygenation
Natural products
Reagents
Thioesters
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 9559
container_issue 41
container_start_page 9555
container_title Chemical science (Cambridge)
container_volume 1
creator Mao, Runze
Bera, Srikrishna
Cheseaux, Alexis
Hu, Xile
description Here we describe a deoxygenative trifluoromethylthiolation method that yields trifluoromethyl thioesters from readily available carboxylic acids. The method is built upon an umpolung strategy where triphenylphosphine is used to first activate an electrophilic trifluoromethylthiolating reagent and then serves as an oxygen acceptor for the deoxygenation. The method is mild, efficient, broad-scope, and tolerant. It can be applied for the late-stage functionalization of numerous natural products and drug molecules containing a carboxylic acid group. The trifluoromethyl thioesters can be converted into trifluoromethyl thioethers by Pd-catalyzed decarbonylation. A deoxygenative trifluoromethylthiolation method produces trifluoromethyl thioesters from readily available carboxylic acids.
doi_str_mv 10.1039/c9sc03396c
format Article
fullrecord <record><control><sourceid>proquest_rsc_p</sourceid><recordid>TN_cdi_rsc_primary_c9sc03396c</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2355938984</sourcerecordid><originalsourceid>FETCH-LOGICAL-c428t-6cecd02759771b047d06af0734c6533f0bd82c32a9c6b1d34745fb8d232c27f93</originalsourceid><addsrcrecordid>eNpdkc1LxDAQxYMorqgX78qCFxFW00zaNAiC1E8QPKjnkE7T3SzdZk1acf97o6vrx1xm4P14vOERspfQk4SCPEUZkALIDNfIFqM8GWUpyPXVzeiA7IYwpXEAkpSJTTIARtMUmNgiZ5fGvS3GptWdfTXDztu66Z13M9NNFk03sa6JimuHrh6i9mWEG4tDjbYKO2Sj1k0wu197mzxfXz0Vt6P7h5u74uJ-hJzl3ShDgxVlIpVCJCXloqKZrqkAjjEq1LSscobAtMSsTCrggqd1mVcMGDJRS9gm50vfeV_OTIWm7bxu1NzbmfYL5bRVf5XWTtTYvapMCskljwZHXwbevfQmdGpmA5qm0a1xfVAM0lRCLvMP9PAfOnW9b-N7kaJ5EoeLSB0vKfQuBG_qVZiEqo9aVCEfi89aiggf_I6_Qr9LiMD-EvABV-pPr_AOaO2SKQ</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2308111147</pqid></control><display><type>article</type><title>Deoxygenative trifluoromethylthiolation of carboxylic acids</title><source>DOAJ Directory of Open Access Journals</source><source>EZB-FREE-00999 freely available EZB journals</source><source>PubMed Central</source><source>PubMed Central Open Access</source><creator>Mao, Runze ; Bera, Srikrishna ; Cheseaux, Alexis ; Hu, Xile</creator><creatorcontrib>Mao, Runze ; Bera, Srikrishna ; Cheseaux, Alexis ; Hu, Xile</creatorcontrib><description>Here we describe a deoxygenative trifluoromethylthiolation method that yields trifluoromethyl thioesters from readily available carboxylic acids. The method is built upon an umpolung strategy where triphenylphosphine is used to first activate an electrophilic trifluoromethylthiolating reagent and then serves as an oxygen acceptor for the deoxygenation. The method is mild, efficient, broad-scope, and tolerant. It can be applied for the late-stage functionalization of numerous natural products and drug molecules containing a carboxylic acid group. The trifluoromethyl thioesters can be converted into trifluoromethyl thioethers by Pd-catalyzed decarbonylation. A deoxygenative trifluoromethylthiolation method produces trifluoromethyl thioesters from readily available carboxylic acids.</description><identifier>ISSN: 2041-6520</identifier><identifier>EISSN: 2041-6539</identifier><identifier>DOI: 10.1039/c9sc03396c</identifier><identifier>PMID: 32055327</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Carboxylic acids ; Chemistry ; Deoxygenation ; Natural products ; Reagents ; Thioesters</subject><ispartof>Chemical science (Cambridge), 2019-11, Vol.1 (41), p.9555-9559</ispartof><rights>This journal is © The Royal Society of Chemistry 2019.</rights><rights>Copyright Royal Society of Chemistry 2019</rights><rights>This journal is © The Royal Society of Chemistry 2019 2019</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c428t-6cecd02759771b047d06af0734c6533f0bd82c32a9c6b1d34745fb8d232c27f93</citedby><cites>FETCH-LOGICAL-c428t-6cecd02759771b047d06af0734c6533f0bd82c32a9c6b1d34745fb8d232c27f93</cites><orcidid>0000-0001-8335-1196 ; 0000-0003-4678-7251</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC6979494/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC6979494/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,860,881,27901,27902,53766,53768</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32055327$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Mao, Runze</creatorcontrib><creatorcontrib>Bera, Srikrishna</creatorcontrib><creatorcontrib>Cheseaux, Alexis</creatorcontrib><creatorcontrib>Hu, Xile</creatorcontrib><title>Deoxygenative trifluoromethylthiolation of carboxylic acids</title><title>Chemical science (Cambridge)</title><addtitle>Chem Sci</addtitle><description>Here we describe a deoxygenative trifluoromethylthiolation method that yields trifluoromethyl thioesters from readily available carboxylic acids. The method is built upon an umpolung strategy where triphenylphosphine is used to first activate an electrophilic trifluoromethylthiolating reagent and then serves as an oxygen acceptor for the deoxygenation. The method is mild, efficient, broad-scope, and tolerant. It can be applied for the late-stage functionalization of numerous natural products and drug molecules containing a carboxylic acid group. The trifluoromethyl thioesters can be converted into trifluoromethyl thioethers by Pd-catalyzed decarbonylation. A deoxygenative trifluoromethylthiolation method produces trifluoromethyl thioesters from readily available carboxylic acids.</description><subject>Carboxylic acids</subject><subject>Chemistry</subject><subject>Deoxygenation</subject><subject>Natural products</subject><subject>Reagents</subject><subject>Thioesters</subject><issn>2041-6520</issn><issn>2041-6539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNpdkc1LxDAQxYMorqgX78qCFxFW00zaNAiC1E8QPKjnkE7T3SzdZk1acf97o6vrx1xm4P14vOERspfQk4SCPEUZkALIDNfIFqM8GWUpyPXVzeiA7IYwpXEAkpSJTTIARtMUmNgiZ5fGvS3GptWdfTXDztu66Z13M9NNFk03sa6JimuHrh6i9mWEG4tDjbYKO2Sj1k0wu197mzxfXz0Vt6P7h5u74uJ-hJzl3ShDgxVlIpVCJCXloqKZrqkAjjEq1LSscobAtMSsTCrggqd1mVcMGDJRS9gm50vfeV_OTIWm7bxu1NzbmfYL5bRVf5XWTtTYvapMCskljwZHXwbevfQmdGpmA5qm0a1xfVAM0lRCLvMP9PAfOnW9b-N7kaJ5EoeLSB0vKfQuBG_qVZiEqo9aVCEfi89aiggf_I6_Qr9LiMD-EvABV-pPr_AOaO2SKQ</recordid><startdate>20191107</startdate><enddate>20191107</enddate><creator>Mao, Runze</creator><creator>Bera, Srikrishna</creator><creator>Cheseaux, Alexis</creator><creator>Hu, Xile</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0001-8335-1196</orcidid><orcidid>https://orcid.org/0000-0003-4678-7251</orcidid></search><sort><creationdate>20191107</creationdate><title>Deoxygenative trifluoromethylthiolation of carboxylic acids</title><author>Mao, Runze ; Bera, Srikrishna ; Cheseaux, Alexis ; Hu, Xile</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c428t-6cecd02759771b047d06af0734c6533f0bd82c32a9c6b1d34745fb8d232c27f93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Carboxylic acids</topic><topic>Chemistry</topic><topic>Deoxygenation</topic><topic>Natural products</topic><topic>Reagents</topic><topic>Thioesters</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mao, Runze</creatorcontrib><creatorcontrib>Bera, Srikrishna</creatorcontrib><creatorcontrib>Cheseaux, Alexis</creatorcontrib><creatorcontrib>Hu, Xile</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Chemical science (Cambridge)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mao, Runze</au><au>Bera, Srikrishna</au><au>Cheseaux, Alexis</au><au>Hu, Xile</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Deoxygenative trifluoromethylthiolation of carboxylic acids</atitle><jtitle>Chemical science (Cambridge)</jtitle><addtitle>Chem Sci</addtitle><date>2019-11-07</date><risdate>2019</risdate><volume>1</volume><issue>41</issue><spage>9555</spage><epage>9559</epage><pages>9555-9559</pages><issn>2041-6520</issn><eissn>2041-6539</eissn><abstract>Here we describe a deoxygenative trifluoromethylthiolation method that yields trifluoromethyl thioesters from readily available carboxylic acids. The method is built upon an umpolung strategy where triphenylphosphine is used to first activate an electrophilic trifluoromethylthiolating reagent and then serves as an oxygen acceptor for the deoxygenation. The method is mild, efficient, broad-scope, and tolerant. It can be applied for the late-stage functionalization of numerous natural products and drug molecules containing a carboxylic acid group. The trifluoromethyl thioesters can be converted into trifluoromethyl thioethers by Pd-catalyzed decarbonylation. A deoxygenative trifluoromethylthiolation method produces trifluoromethyl thioesters from readily available carboxylic acids.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>32055327</pmid><doi>10.1039/c9sc03396c</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0001-8335-1196</orcidid><orcidid>https://orcid.org/0000-0003-4678-7251</orcidid><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 2041-6520
ispartof Chemical science (Cambridge), 2019-11, Vol.1 (41), p.9555-9559
issn 2041-6520
2041-6539
language eng
recordid cdi_rsc_primary_c9sc03396c
source DOAJ Directory of Open Access Journals; EZB-FREE-00999 freely available EZB journals; PubMed Central; PubMed Central Open Access
subjects Carboxylic acids
Chemistry
Deoxygenation
Natural products
Reagents
Thioesters
title Deoxygenative trifluoromethylthiolation of carboxylic acids
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-04T13%3A20%3A36IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_rsc_p&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Deoxygenative%20trifluoromethylthiolation%20of%20carboxylic%20acids&rft.jtitle=Chemical%20science%20(Cambridge)&rft.au=Mao,%20Runze&rft.date=2019-11-07&rft.volume=1&rft.issue=41&rft.spage=9555&rft.epage=9559&rft.pages=9555-9559&rft.issn=2041-6520&rft.eissn=2041-6539&rft_id=info:doi/10.1039/c9sc03396c&rft_dat=%3Cproquest_rsc_p%3E2355938984%3C/proquest_rsc_p%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2308111147&rft_id=info:pmid/32055327&rfr_iscdi=true