Litcius/Paper detail

Salicylaldehyde-Cobalt(II)-Catalyzed C–H Alkoxylation of Indoles with Secondary Alcohols

Mao‐Gui Huang, Yuyan Tan, M. AI, Xiao-Hong Chen, Hai‐Bing Xu, Yue‐Jin Liu

2024The Journal of Organic Chemistry10 citationsDOI

Abstract

A straight and efficient protocol for the synthesis of hindered indole-ethers via C-H alkoxylation of indoles was developed by a cobalt-catalyzed cross-dehydrogenative coupling reaction with secondary alcohols. The selection of the salicylaldehyde-Co(II) catalyst enables the reaction to proceed under conditions without acid or base addition in the presence of limited alcohols. The protocol has broad substrate scope for both indole and secondary alcohols and exhibits good functional tolerance. The synthetic applications are proven by gram-scale reaction and further diversification of the product. Preliminary mechanistic investigations indicate that the activation of C-H bonds is not the rate-determining step of the reaction.

Topics & Concepts

ChemistrySalicylaldehydeCobaltCatalysisOrganic chemistryMedicinal chemistryPolymer chemistrySchiff baseCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsOxidative Organic Chemistry Reactions