Rhodium-Catalyzed Regioselective C7-Functionalization of N-Pivaloylindoles

Lanting Xu; Chao Zhang; Yupeng He; Lushi Tan; Dawei Ma

doi:10.1002/anie.201508117

Rhodium-Catalyzed Regioselective C7-Functionalization of N-Pivaloylindoles

Angew Chem Int Ed Engl. 2016 Jan 4;55(1):321-5. doi: 10.1002/anie.201508117. Epub 2015 Oct 29.

Authors

Lanting Xu¹, Chao Zhang², Yupeng He², Lushi Tan³, Dawei Ma⁴

Affiliations

¹ State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032 (China).
² Liaoning Shihua University, Dandong Lu West 1, Fushun 113001 (China).
³ Merck Research Laboratories, P.O. Box 2000, RY800-D280, Rahway, NJ 07065-0900 (USA). lushi_tan@merck.com.
⁴ State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032 (China). madw@mail.sioc.ac.cn.

PMID: 26510833
DOI: 10.1002/anie.201508117

Abstract

An efficient rhodium-catalyzed method for direct C-H functionalization at the C7 position of a wide range of indoles has been developed. Good to excellent yields of alkenylation products were observed with acrylates, styrenes, and vinyl phenyl sulfones, whereas the saturated alkylation products were obtained in good yield with α,β-unsaturated ketones. Both the N-pivaloyl directing group and the rhodium catalyst proved to be crucial for high regioselectivity and conversion.

Keywords: CH activation; alkenylation; homogeneous catalysis; indoles; rhodium.

Publication types

Research Support, Non-U.S. Gov't