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Nickel-catalyzed decarbonylation of N-acylated N-heteroarenes†
Toshifumi Morioka,Syun Nakatani,Yuki Sakamoto,Takuya Kodama,Sensuke Ogoshi,Naoto Chatani,Mamoru Tobisu
Chemical Science Pub Date : 05/29/2019 00:00:00 , DOI:10.1039/C9SC02035G
Abstract

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.

Graphical abstract: Nickel-catalyzed decarbonylation of N-acylated N-heteroarenes
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