Broad-Scope Rh-Catalyzed Inverse-Sonogashira Reaction Directed by Weakly Coordinating Groups

[Image: see text] We report the alkynylation of C(sp(2))–H bonds with bromoalkynes (inverse-Sonogashira reaction) directed by synthetically useful ester, ketone, and ether groups under rhodium catalysis. Other less common directing groups such as amine, thioether, sulfoxide, sulfone, phenol ester, a...

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Autores principales: Tan, Eric, Quinonero, Ophélie, Elena de Orbe, M., Echavarren, Antonio M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5838643/
https://www.ncbi.nlm.nih.gov/pubmed/29527402
http://dx.doi.org/10.1021/acscatal.7b04395
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author Tan, Eric
Quinonero, Ophélie
Elena de Orbe, M.
Echavarren, Antonio M.
author_facet Tan, Eric
Quinonero, Ophélie
Elena de Orbe, M.
Echavarren, Antonio M.
author_sort Tan, Eric
collection PubMed
description [Image: see text] We report the alkynylation of C(sp(2))–H bonds with bromoalkynes (inverse-Sonogashira reaction) directed by synthetically useful ester, ketone, and ether groups under rhodium catalysis. Other less common directing groups such as amine, thioether, sulfoxide, sulfone, phenol ester, and carbamate are also suitable directing groups. Mechanistic studies indicate that the reaction proceeds by a turnover-limiting C–H activation step via an electrophilic-type substitution.
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spelling pubmed-58386432018-03-07 Broad-Scope Rh-Catalyzed Inverse-Sonogashira Reaction Directed by Weakly Coordinating Groups Tan, Eric Quinonero, Ophélie Elena de Orbe, M. Echavarren, Antonio M. ACS Catal [Image: see text] We report the alkynylation of C(sp(2))–H bonds with bromoalkynes (inverse-Sonogashira reaction) directed by synthetically useful ester, ketone, and ether groups under rhodium catalysis. Other less common directing groups such as amine, thioether, sulfoxide, sulfone, phenol ester, and carbamate are also suitable directing groups. Mechanistic studies indicate that the reaction proceeds by a turnover-limiting C–H activation step via an electrophilic-type substitution. American Chemical Society 2018-01-29 2018-03-02 /pmc/articles/PMC5838643/ /pubmed/29527402 http://dx.doi.org/10.1021/acscatal.7b04395 Text en Copyright © 2018 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Tan, Eric
Quinonero, Ophélie
Elena de Orbe, M.
Echavarren, Antonio M.
Broad-Scope Rh-Catalyzed Inverse-Sonogashira Reaction Directed by Weakly Coordinating Groups
title Broad-Scope Rh-Catalyzed Inverse-Sonogashira Reaction Directed by Weakly Coordinating Groups
title_full Broad-Scope Rh-Catalyzed Inverse-Sonogashira Reaction Directed by Weakly Coordinating Groups
title_fullStr Broad-Scope Rh-Catalyzed Inverse-Sonogashira Reaction Directed by Weakly Coordinating Groups
title_full_unstemmed Broad-Scope Rh-Catalyzed Inverse-Sonogashira Reaction Directed by Weakly Coordinating Groups
title_short Broad-Scope Rh-Catalyzed Inverse-Sonogashira Reaction Directed by Weakly Coordinating Groups
title_sort broad-scope rh-catalyzed inverse-sonogashira reaction directed by weakly coordinating groups
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5838643/
https://www.ncbi.nlm.nih.gov/pubmed/29527402
http://dx.doi.org/10.1021/acscatal.7b04395
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AT quinoneroophelie broadscoperhcatalyzedinversesonogashirareactiondirectedbyweaklycoordinatinggroups
AT elenadeorbem broadscoperhcatalyzedinversesonogashirareactiondirectedbyweaklycoordinatinggroups
AT echavarrenantoniom broadscoperhcatalyzedinversesonogashirareactiondirectedbyweaklycoordinatinggroups

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