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

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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.… Click to show full 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.

Keywords: amino nitro; benzyl alcohols; nitro benzyl; cyclization amino; cyclization; substituted quinolines

Journal Title: ChemCatChem
Year Published: 2023

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