Rhodium-Catalyzed Regioselective C7-Functionalization of N-Pivaloylindoles.
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.
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032 (China).
Lanting
L
Xu
Liaoning Shihua University, Dandong Lu West 1, Fushun 113001 (China).
Chao
C
Zhang
Liaoning Shihua University, Dandong Lu West 1, Fushun 113001 (China).
Yupeng
Y
He
Merck Research Laboratories, P.O. Box 2000, RY800-D280, Rahway, NJ 07065-0900 (USA). lushi_tan@merck.com.
Lushi
L
Tan
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.
Dawei
D
Ma
CH activation; alkenylation; homogeneous catalysis; indoles; rhodium