Efficient Copper-Catalysed Synthesis of Carbazoles by Double N-Arylation of Primary Amines with 2,2'-Dibromobiphenyl in the Presence of Air

Ha Nam Do, Nguyen Minh Quan, Ban Van Phuc, Dinh Van Tinh, Nguyen Quyet Tien, Truong Thi Thanh Nga, Van Tuyen Nguyen, Tran Quang Hung*, Tuan Thanh Dang*, Peter Langer*

*VNU, 19-Le Thanh Tong, Hanoi, Vietnam; VAST, 18-Hoang Quoc Viet, Hanoi, Vietnam; Univ. Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany, Email: dangthanhtuanhus.edu.vn, tqhungich.vast.vn, peter.langeruni-rostock.de

H. N. Do, N. M. Quan, B. V. Phuc, D. V. Tinh, N. Q. Tien, T. T. T. Nga, V. T. Nguyen, T. Q. Hung, T. T. Dang, P. Langer, J. An, Synlett, 2021, 32, 611-615.

DOI: 10.1055/s-0040-1706641

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Abstract

Double Cu-catalyzed C-N coupling reactions of 2,2'-dibromobiphenyl and amines enable an efficient synthesis of carbazole derivatives in the presence of air. The reaction is robust, proceeds in high yields, and tolerates a series of amines including neutral, electron-rich, electron-deficient aromatic amines and aliphatic amines.

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Key Words

Cu catalysis, carbazole synthesis, C-N coupling, sustainable process

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ID: J72-Y2021