Benzene construction via Pd-catalyzed cyclization of 2,7-alkadiynylic carbonates in the presence of alkynes

A palladium-catalyzed highly regio- and chemo-selective cyclization of 2,7-alkadiynylic carbonates with functionalized alkynes to construct 1,3-dihydroisobenzofuran and isoindoline derivatives under mild conditions has been developed. Functional groups such as alcohol, sulfonamide, and indoles could...

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Autores principales: Zhang, Yuchen, Wu, Wangteng, Fu, Chunling, Huang, Xin, Ma, Shengming
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2018
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6385558/
https://www.ncbi.nlm.nih.gov/pubmed/30881648
http://dx.doi.org/10.1039/c8sc04681f
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author Zhang, Yuchen
Wu, Wangteng
Fu, Chunling
Huang, Xin
Ma, Shengming
author_facet Zhang, Yuchen
Wu, Wangteng
Fu, Chunling
Huang, Xin
Ma, Shengming
author_sort Zhang, Yuchen
collection PubMed
description A palladium-catalyzed highly regio- and chemo-selective cyclization of 2,7-alkadiynylic carbonates with functionalized alkynes to construct 1,3-dihydroisobenzofuran and isoindoline derivatives under mild conditions has been developed. Functional groups such as alcohol, sulfonamide, and indoles could be well tolerated. After careful mechanistic studies, a mechanism involving oxidative addition and regioselectivity-defined double alkyne insertions has been proposed.
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spelling pubmed-63855582019-03-15 Benzene construction via Pd-catalyzed cyclization of 2,7-alkadiynylic carbonates in the presence of alkynes Zhang, Yuchen Wu, Wangteng Fu, Chunling Huang, Xin Ma, Shengming Chem Sci Chemistry A palladium-catalyzed highly regio- and chemo-selective cyclization of 2,7-alkadiynylic carbonates with functionalized alkynes to construct 1,3-dihydroisobenzofuran and isoindoline derivatives under mild conditions has been developed. Functional groups such as alcohol, sulfonamide, and indoles could be well tolerated. After careful mechanistic studies, a mechanism involving oxidative addition and regioselectivity-defined double alkyne insertions has been proposed. Royal Society of Chemistry 2018-12-19 /pmc/articles/PMC6385558/ /pubmed/30881648 http://dx.doi.org/10.1039/c8sc04681f Text en This journal is © The Royal Society of Chemistry 2019 https://creativecommons.org/licenses/by/3.0/This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Zhang, Yuchen
Wu, Wangteng
Fu, Chunling
Huang, Xin
Ma, Shengming
Benzene construction via Pd-catalyzed cyclization of 2,7-alkadiynylic carbonates in the presence of alkynes
title Benzene construction via Pd-catalyzed cyclization of 2,7-alkadiynylic carbonates in the presence of alkynes
title_full Benzene construction via Pd-catalyzed cyclization of 2,7-alkadiynylic carbonates in the presence of alkynes
title_fullStr Benzene construction via Pd-catalyzed cyclization of 2,7-alkadiynylic carbonates in the presence of alkynes
title_full_unstemmed Benzene construction via Pd-catalyzed cyclization of 2,7-alkadiynylic carbonates in the presence of alkynes
title_short Benzene construction via Pd-catalyzed cyclization of 2,7-alkadiynylic carbonates in the presence of alkynes
title_sort benzene construction via pd-catalyzed cyclization of 2,7-alkadiynylic carbonates in the presence of alkynes
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6385558/
https://www.ncbi.nlm.nih.gov/pubmed/30881648
http://dx.doi.org/10.1039/c8sc04681f
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