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

Intermolecular Cyclization to N-heteroarene: Sequential de hydrogenative coupling of two different primary alcohols to C-3-substituted quinolines is presented using nickel catalysis.

Abstract

We 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.

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