Ru()-catalyzed external auxiliary-free primary amide-directed inverse Sonogashira reaction on (hetero)arylamides

Herein, we report ruthenium( ii )-catalyzed weakly coordinating primary amide-assisted ortho -di-alkynylation of (hetero)arylamides via double C-H bond activation in the presence of bromo-alkynes as coupling partners. The attractive features of the developed strategy lie in the usage of an inexpensi...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Chemical communications (Cambridge, England) England), 2022-10, Vol.58 (8), p.1134-1137
Hauptverfasser: Baghel, Akanksha Singh, Kumar, Amit
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 1137
container_issue 8
container_start_page 1134
container_title Chemical communications (Cambridge, England)
container_volume 58
creator Baghel, Akanksha Singh
Kumar, Amit
description Herein, we report ruthenium( ii )-catalyzed weakly coordinating primary amide-assisted ortho -di-alkynylation of (hetero)arylamides via double C-H bond activation in the presence of bromo-alkynes as coupling partners. The attractive features of the developed strategy lie in the usage of an inexpensive ruthenium( ii )-salt, external auxiliary-free directing group and simple reaction conditions, along with a broad substrate scope, high reaction yields and scale-up synthesis. An effective protocol has been developed for the mono/di-alkynylation of (hetero)arylamides via double C-H bond activation with bromo-alkynes as coupling partners using the primary amide as a directing group in the presence of a ruthenium( ii )-salt.
doi_str_mv 10.1039/d2cc03929j
format Article
fullrecord <record><control><sourceid>proquest_rsc_p</sourceid><recordid>TN_cdi_proquest_miscellaneous_2716088596</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2721635700</sourcerecordid><originalsourceid>FETCH-LOGICAL-c244t-ee1c5a8b6e0c65094d49c5b9fad6b406b22569b7d7b2d002c619750b6878088e3</originalsourceid><addsrcrecordid>eNpd0c9LwzAUB_AiCs7pxbtQ8LIJ0SRN0uYo9TeC4A_wVtLkzWV07Uxa2fzrTbehYAi8F_i8d_gmio4JPic4kReGah0qlbOdaEASwRBn2ftu33OJ0oTx_ejA-xkOh_BsEC2eu9EYadWqavUNJoZlC65WVay6pa2scis0cQDxwtl5eMRqbg0gYx3oNnBbf4HzEL80dfOh_NQ6FTtQurVNHYc7mkLY14zDaLUe9YfR3kRVHo62dRi93Vy_5nfo8en2Pr98RJoy1iIAornKSgFYC44lM0xqXsqJMqJkWJSUciHL1KQlNRhTLYhMOS5FlmY4yyAZRqPN3oVrPjvwbTG3XkNVqRqazhc0JSJALkWgp__orOn6EHpFiUh4inFQZxulXeO9g0mxzaQguOjDL65onq_Dfwj4ZIOd17_u73OSH5XIgcc</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2721635700</pqid></control><display><type>article</type><title>Ru()-catalyzed external auxiliary-free primary amide-directed inverse Sonogashira reaction on (hetero)arylamides</title><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Baghel, Akanksha Singh ; Kumar, Amit</creator><creatorcontrib>Baghel, Akanksha Singh ; Kumar, Amit</creatorcontrib><description>Herein, we report ruthenium( ii )-catalyzed weakly coordinating primary amide-assisted ortho -di-alkynylation of (hetero)arylamides via double C-H bond activation in the presence of bromo-alkynes as coupling partners. The attractive features of the developed strategy lie in the usage of an inexpensive ruthenium( ii )-salt, external auxiliary-free directing group and simple reaction conditions, along with a broad substrate scope, high reaction yields and scale-up synthesis. An effective protocol has been developed for the mono/di-alkynylation of (hetero)arylamides via double C-H bond activation with bromo-alkynes as coupling partners using the primary amide as a directing group in the presence of a ruthenium( ii )-salt.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/d2cc03929j</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Alkynes ; Chemical synthesis ; Hydrogen bonds ; Ruthenium ; Ruthenium compounds ; Substrates</subject><ispartof>Chemical communications (Cambridge, England), 2022-10, Vol.58 (8), p.1134-1137</ispartof><rights>Copyright Royal Society of Chemistry 2022</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c244t-ee1c5a8b6e0c65094d49c5b9fad6b406b22569b7d7b2d002c619750b6878088e3</citedby><cites>FETCH-LOGICAL-c244t-ee1c5a8b6e0c65094d49c5b9fad6b406b22569b7d7b2d002c619750b6878088e3</cites><orcidid>0000-0002-1683-7740</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></links><search><creatorcontrib>Baghel, Akanksha Singh</creatorcontrib><creatorcontrib>Kumar, Amit</creatorcontrib><title>Ru()-catalyzed external auxiliary-free primary amide-directed inverse Sonogashira reaction on (hetero)arylamides</title><title>Chemical communications (Cambridge, England)</title><description>Herein, we report ruthenium( ii )-catalyzed weakly coordinating primary amide-assisted ortho -di-alkynylation of (hetero)arylamides via double C-H bond activation in the presence of bromo-alkynes as coupling partners. The attractive features of the developed strategy lie in the usage of an inexpensive ruthenium( ii )-salt, external auxiliary-free directing group and simple reaction conditions, along with a broad substrate scope, high reaction yields and scale-up synthesis. An effective protocol has been developed for the mono/di-alkynylation of (hetero)arylamides via double C-H bond activation with bromo-alkynes as coupling partners using the primary amide as a directing group in the presence of a ruthenium( ii )-salt.</description><subject>Alkynes</subject><subject>Chemical synthesis</subject><subject>Hydrogen bonds</subject><subject>Ruthenium</subject><subject>Ruthenium compounds</subject><subject>Substrates</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpd0c9LwzAUB_AiCs7pxbtQ8LIJ0SRN0uYo9TeC4A_wVtLkzWV07Uxa2fzrTbehYAi8F_i8d_gmio4JPic4kReGah0qlbOdaEASwRBn2ftu33OJ0oTx_ejA-xkOh_BsEC2eu9EYadWqavUNJoZlC65WVay6pa2scis0cQDxwtl5eMRqbg0gYx3oNnBbf4HzEL80dfOh_NQ6FTtQurVNHYc7mkLY14zDaLUe9YfR3kRVHo62dRi93Vy_5nfo8en2Pr98RJoy1iIAornKSgFYC44lM0xqXsqJMqJkWJSUciHL1KQlNRhTLYhMOS5FlmY4yyAZRqPN3oVrPjvwbTG3XkNVqRqazhc0JSJALkWgp__orOn6EHpFiUh4inFQZxulXeO9g0mxzaQguOjDL65onq_Dfwj4ZIOd17_u73OSH5XIgcc</recordid><startdate>20221006</startdate><enddate>20221006</enddate><creator>Baghel, Akanksha Singh</creator><creator>Kumar, Amit</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-1683-7740</orcidid></search><sort><creationdate>20221006</creationdate><title>Ru()-catalyzed external auxiliary-free primary amide-directed inverse Sonogashira reaction on (hetero)arylamides</title><author>Baghel, Akanksha Singh ; Kumar, Amit</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c244t-ee1c5a8b6e0c65094d49c5b9fad6b406b22569b7d7b2d002c619750b6878088e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Alkynes</topic><topic>Chemical synthesis</topic><topic>Hydrogen bonds</topic><topic>Ruthenium</topic><topic>Ruthenium compounds</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Baghel, Akanksha Singh</creatorcontrib><creatorcontrib>Kumar, Amit</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Baghel, Akanksha Singh</au><au>Kumar, Amit</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Ru()-catalyzed external auxiliary-free primary amide-directed inverse Sonogashira reaction on (hetero)arylamides</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><date>2022-10-06</date><risdate>2022</risdate><volume>58</volume><issue>8</issue><spage>1134</spage><epage>1137</epage><pages>1134-1137</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>Herein, we report ruthenium( ii )-catalyzed weakly coordinating primary amide-assisted ortho -di-alkynylation of (hetero)arylamides via double C-H bond activation in the presence of bromo-alkynes as coupling partners. The attractive features of the developed strategy lie in the usage of an inexpensive ruthenium( ii )-salt, external auxiliary-free directing group and simple reaction conditions, along with a broad substrate scope, high reaction yields and scale-up synthesis. An effective protocol has been developed for the mono/di-alkynylation of (hetero)arylamides via double C-H bond activation with bromo-alkynes as coupling partners using the primary amide as a directing group in the presence of a ruthenium( ii )-salt.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d2cc03929j</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-1683-7740</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1359-7345
ispartof Chemical communications (Cambridge, England), 2022-10, Vol.58 (8), p.1134-1137
issn 1359-7345
1364-548X
language eng
recordid cdi_proquest_miscellaneous_2716088596
source Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects Alkynes
Chemical synthesis
Hydrogen bonds
Ruthenium
Ruthenium compounds
Substrates
title Ru()-catalyzed external auxiliary-free primary amide-directed inverse Sonogashira reaction on (hetero)arylamides
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-04T16%3A21%3A06IST&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=Ru()-catalyzed%20external%20auxiliary-free%20primary%20amide-directed%20inverse%20Sonogashira%20reaction%20on%20(hetero)arylamides&rft.jtitle=Chemical%20communications%20(Cambridge,%20England)&rft.au=Baghel,%20Akanksha%20Singh&rft.date=2022-10-06&rft.volume=58&rft.issue=8&rft.spage=1134&rft.epage=1137&rft.pages=1134-1137&rft.issn=1359-7345&rft.eissn=1364-548X&rft_id=info:doi/10.1039/d2cc03929j&rft_dat=%3Cproquest_rsc_p%3E2721635700%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=2721635700&rft_id=info:pmid/&rfr_iscdi=true