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Nickel-catalyzed decarbonylation of N-acylated N-heteroarenes. 2019
Toshifumi Morioka, and
Syun Nakatani, and
Yuki Sakamoto, and
Takuya Kodama, and
Sensuke Ogoshi, and
Naoto Chatani, and
Mamoru Tobisu
Department of Applied Chemistry , Faculty of Engineering , Osaka University , Suita , Osaka 565-0871 , Japan . Email: tobisu@chem.eng.osaka-u.ac.jp ; Email: chatani@chem.eng.osaka-u.ac.jp.
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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