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Nickel-catalyzed decarbonylation of N-acylated N-heteroarenes.

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.

SUBMITTER: Morioka T

PROVIDER: S-EPMC6625484 | biostudies-literature | 2019 Jul

REPOSITORIES: biostudies-literature

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Nickel-catalyzed decarbonylation of N-acylated N-heteroarenes.

Morioka Toshifumi T Nakatani Syun S Sakamoto Yuki Y Kodama Takuya T Ogoshi Sensuke S Chatani Naoto N Tobisu Mamoru M

Chemical science 20190529 27

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 for ...[more]

PMID: 31367320

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