Nickel-catalyzed decarbonylation of N-acylated N-heteroarenes

Nickel-catalyzed decarbonylation of N-acylated N-heteroarenes is developed. This method can be used to produce a variety of N-aryl heteroarenes, including pyrroles, indoles, carbazoles and phenoxazines, using benzoic acid derivatives as arylating reagents. Arylnickelamide intermediates that are rele...

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Autores principales: Morioka, Toshifumi, Nakatani, Syun, Sakamoto, Yuki, Kodama, Takuya, Ogoshi, Sensuke, Chatani, Naoto, Tobisu, Mamoru
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6625484/
https://www.ncbi.nlm.nih.gov/pubmed/31367320
http://dx.doi.org/10.1039/c9sc02035g
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author Morioka, Toshifumi
Nakatani, Syun
Sakamoto, Yuki
Kodama, Takuya
Ogoshi, Sensuke
Chatani, Naoto
Tobisu, Mamoru
author_facet Morioka, Toshifumi
Nakatani, Syun
Sakamoto, Yuki
Kodama, Takuya
Ogoshi, Sensuke
Chatani, Naoto
Tobisu, Mamoru
author_sort Morioka, Toshifumi
collection PubMed
description Nickel-catalyzed decarbonylation of N-acylated N-heteroarenes is developed. This method can be used to produce a variety of N-aryl heteroarenes, including pyrroles, indoles, carbazoles and phenoxazines, using benzoic acid derivatives as arylating reagents. Arylnickelamide intermediates that are relevant to the catalytic reaction were characterized by X-ray crystallography. When N-acylated benzimidazoles are used as substrates, decarbonylation accompanied 1,2-migration to form 2-arylated benzimidazoles.
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spelling pubmed-66254842019-07-31 Nickel-catalyzed decarbonylation of N-acylated N-heteroarenes Morioka, Toshifumi Nakatani, Syun Sakamoto, Yuki Kodama, Takuya Ogoshi, Sensuke Chatani, Naoto Tobisu, Mamoru Chem Sci Chemistry Nickel-catalyzed decarbonylation of N-acylated N-heteroarenes is developed. This method can be used to produce a variety of N-aryl heteroarenes, including pyrroles, indoles, carbazoles and phenoxazines, using benzoic acid derivatives as arylating reagents. Arylnickelamide intermediates that are relevant to the catalytic reaction were characterized by X-ray crystallography. When N-acylated benzimidazoles are used as substrates, decarbonylation accompanied 1,2-migration to form 2-arylated benzimidazoles. Royal Society of Chemistry 2019-05-29 /pmc/articles/PMC6625484/ /pubmed/31367320 http://dx.doi.org/10.1039/c9sc02035g Text en This journal is © The Royal Society of Chemistry 2019 https://creativecommons.org/licenses/by-nc/3.0/This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0)
spellingShingle Chemistry
Morioka, Toshifumi
Nakatani, Syun
Sakamoto, Yuki
Kodama, Takuya
Ogoshi, Sensuke
Chatani, Naoto
Tobisu, Mamoru
Nickel-catalyzed decarbonylation of N-acylated N-heteroarenes
title Nickel-catalyzed decarbonylation of N-acylated N-heteroarenes
title_full Nickel-catalyzed decarbonylation of N-acylated N-heteroarenes
title_fullStr Nickel-catalyzed decarbonylation of N-acylated N-heteroarenes
title_full_unstemmed Nickel-catalyzed decarbonylation of N-acylated N-heteroarenes
title_short Nickel-catalyzed decarbonylation of N-acylated N-heteroarenes
title_sort nickel-catalyzed decarbonylation of n-acylated n-heteroarenes
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6625484/
https://www.ncbi.nlm.nih.gov/pubmed/31367320
http://dx.doi.org/10.1039/c9sc02035g
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