Synlett
DOI: 10.1055/s-0036-1588530
letter
© Georg Thieme Verlag Stuttgart · New York

Rhodium-Catalyzed Regioselective C7-Functionalization of Indole Derivatives with Acrylates by Using an N-Imino Directing Group

Lanting Xua, Lushi Tan*b, Dawei Ma*c
  • aShanghai Research Institute of Fragrance and Flavor Industry, 480 Nanning Road, Shanghai 200232, P. R. of China
  • bMerck Research Laboratories, P.O. Box 2000, RY800-D280, Rahway, NJ 07065-0900, USA   Email: lushi_tan@merck.com
  • cState Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. of China   Email: madw@sioc.ac.cn
We are grateful to the Shanghai Sailing Program (17YF1418900) and Merck for their financial support.
Further Information

Publication History

Received: 07 June 2017

Accepted after revision: 06 July 2017

Publication Date:
17 August 2017 (eFirst)

Dedicated to Professor Victor Snieckus on the occasion of his 80th birthday

Abstract

An efficient rhodium-catalyzed method for C–H olefination at the C7 position of indoles has been developed. The N-imino directing group was shown to be crucial for high regioselectivity and reactivity of the metal catalyst. The utility of this protocol was further demonstrated through a concise, four-step synthesis of pyroquilon from indole.

Supporting Information