Nickel‐Catalyzed Sequential Dehydrogenation and Cyclization of 2‐Amino(Nitro)‐benzyl Alcohols with Alkyl Alcohols: Synthesis of C‐3‐Substituted Quinolines

Abstract

AbstractWe herein reported a general and efficient Ni‐catalyzed protocol for sequential double de‐hydrogenative cyclization of 2‐amino(nitro)‐benzyl alcohols with primary alcohols to C‐3‐substituted quinolines releasing water and dihydrogen as by products. As a special highlight, late stage functionalization of cholesterol derivative including chemo‐selective transformations of citronellol, fatty acid derived oleyl alcohol and long chain C4−C14 alkyl alcohols were reported. Initial mechanistic studies including deuterium‐labelling experiments were perform to establish the de‐hydrogenative cyclization.