Double Heteroatom Functionalization of Arenes Using Benzyne Three‐Component Coupling

Arynes participate in three‐component coupling reactions with N, S, P, and Se functionalities to yield 1,2‐heteroatom‐difunctionalized arenes. Using 2‐iodophenyl arylsulfonates as benzyne precursors, we could effectively add magnesiated S‐, Se‐, and N‐nucleophilic components to the strained triple b...

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Autores principales: García‐López, José‐Antonio, Çetin, Meliha, Greaney, Michael F.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: WILEY‐VCH Verlag 2015
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4832838/
https://www.ncbi.nlm.nih.gov/pubmed/25580700
http://dx.doi.org/10.1002/anie.201410751
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author García‐López, José‐Antonio
Çetin, Meliha
Greaney, Michael F.
author_facet García‐López, José‐Antonio
Çetin, Meliha
Greaney, Michael F.
author_sort García‐López, José‐Antonio
collection PubMed
description Arynes participate in three‐component coupling reactions with N, S, P, and Se functionalities to yield 1,2‐heteroatom‐difunctionalized arenes. Using 2‐iodophenyl arylsulfonates as benzyne precursors, we could effectively add magnesiated S‐, Se‐, and N‐nucleophilic components to the strained triple bond. In the same pot, addition of electrophilic N, S, or P reagents and a copper(I) catalyst trapped the intermediate aryl Grignard to produce a variety of 1,2‐difunctionalized arenes.
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spelling pubmed-48328382016-04-27 Double Heteroatom Functionalization of Arenes Using Benzyne Three‐Component Coupling García‐López, José‐Antonio Çetin, Meliha Greaney, Michael F. Angew Chem Int Ed Engl Communications Arynes participate in three‐component coupling reactions with N, S, P, and Se functionalities to yield 1,2‐heteroatom‐difunctionalized arenes. Using 2‐iodophenyl arylsulfonates as benzyne precursors, we could effectively add magnesiated S‐, Se‐, and N‐nucleophilic components to the strained triple bond. In the same pot, addition of electrophilic N, S, or P reagents and a copper(I) catalyst trapped the intermediate aryl Grignard to produce a variety of 1,2‐difunctionalized arenes. WILEY‐VCH Verlag 2015-01-07 2015-02-09 /pmc/articles/PMC4832838/ /pubmed/25580700 http://dx.doi.org/10.1002/anie.201410751 Text en © 2015 The Authors. Published by Wiley‐VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. Open access.
spellingShingle Communications
García‐López, José‐Antonio
Çetin, Meliha
Greaney, Michael F.
Double Heteroatom Functionalization of Arenes Using Benzyne Three‐Component Coupling
title Double Heteroatom Functionalization of Arenes Using Benzyne Three‐Component Coupling
title_full Double Heteroatom Functionalization of Arenes Using Benzyne Three‐Component Coupling
title_fullStr Double Heteroatom Functionalization of Arenes Using Benzyne Three‐Component Coupling
title_full_unstemmed Double Heteroatom Functionalization of Arenes Using Benzyne Three‐Component Coupling
title_short Double Heteroatom Functionalization of Arenes Using Benzyne Three‐Component Coupling
title_sort double heteroatom functionalization of arenes using benzyne three‐component coupling
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4832838/
https://www.ncbi.nlm.nih.gov/pubmed/25580700
http://dx.doi.org/10.1002/anie.201410751
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