One-step construction of carbazoles by way of the palladium-catalyzed double N-arylation reaction and its application to the total synthesis of murrastifoline-A

• DOI: 10.1016/j.tet.2006.04.087
• Publication Date: 2006-05-22T14:33:59Z
• Authors: Takafumi Kitawaki; Yoko Hayashi; Akiko Ueno; Noritaka Chida
• Keywords: 01 natural sciences; 0104 chemical sciences

Abstract The one-step construction of N-substituted carbazoles by way of the Pd-catalyzed double N-arylation reaction of primary amines with 2,2′-dibromobiphenyl is described. Aryl and aliphatic amines including tert-butylamine and a protected glucopyranosylamine were effectively transformed into the corresponding N-substituted carbazoles. The first total synthesis of murrastifoline-A, a biscarbazole alkaloid, based on this methodology is also presented.