Organic letters

Anionic Indole N-Carbamoyl N→ C Translocation. A Directed remote Metalation Route to 2-Aryl-and 2-Heteroarylindoles. Synthesis of Benz [a] carbazoles and Indeno …

Z Zhao, A Jaworski, I Piel, V Snieckus

Index: Zhao, Zhongdong; Jaworski, Ashley; Piel, Isabel; Snieckus, Victor Organic Letters, 2008 , vol. 10, # 13 p. 2617 - 2620

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Citation Number: 40

Abstract

A new LDA-induced anionic N− C carbamoyl migration of 2-arylindoles (7) is reported. Treatment of N-carbamoylindoles 10 and 13, readily available by direct and ipso- borodesilylative Suzuki− Miyaura cross-coupling routes from 8 and 12, respectively, provides a general route to functionalized 2-arylindoles 11 and 14, respectively (Tables 1 and 2). The reaction has been applied to the synthesis of benzo [a] carbazoles 16 and ...