γ-Carboline synthesis enabled by Rh(<scp>iii</scp>)-catalysed regioselective C–H annulation
Bo Jiang, Jingwen Jia, Yufei Sun, Yichun Wang, Jing Zeng, Xiubin Bu, Liangliang Shi, Xiaoying Sun, Xiaobo Yang
Abstract
A redox-neutral Rh(iii)-catalyzed C-H annulation of indolyl oximes was developed. Relying on the use of various alkynyl silanes as the terminal alkyne surrogates, the reaction exhibited a reverse regioselectivity, thus giving an exclusive and easy way for the synthesis of a wide range of substituent free γ-carbolines at C3 position with high efficiency. Deuterium-labelling experiments and kinetic analysis have preliminarily shed light on the working mode of this catalytic system.
Topics & Concepts
RegioselectivityAnnulationChemistryStereochemistryCombinatorial chemistryCatalysisMedicinal chemistryOrganic chemistryCatalytic C–H Functionalization MethodsSynthesis of Indole DerivativesCatalytic Cross-Coupling Reactions