Rhodium-Catalyzed C−H Functionalization of N-(2-Pyrimidyl)indole with Internal Alkynes: Formation of Unexpected Products by Regulating the Amount of Silver Acetate

Tongyu Li, Zhuo Wang, Chen Chen*(陈晨) and Bolin Zhu*(朱柏林)

Tianjin Key Laboratory of Structure and Performance for Functional Molecules, MOE Key Laboratory of Inorganic-Organic Hybrid Functional Material Chemistry, College of Chemistry, Tianjin Normal University, Tianjin 300387, P. R. China

Adv. Synth. Catal. 2019, 361, 2855-2863.

Abstract: Herein we disclose an uncommon Rhodium(III)-catalyzed C2-selective functionalization of N-(2-Pyrimidyl)indole with internal alkynes. Excess amounts ofsilver acetate (5.0 equiv.) were found to be crucial for the efficient C2 naphthylation and C2 enol esterification of indoles. In sharp contrast, 2.0 equivalents of silver acetate resulted in the C−H alkenylation only. Control experiments were also carried out to briefly study the mechanism of this transformation.

链接：https://onlinelibrary.wiley.com/doi/10.1002/adsc.201900105