Manganese‐Catalyzed Chemoselective Coupling of Secondary Alcohols, Primary Alcohols and Methanol

• Published in: Angewandte Chemie International Edition Vol. 62; no. 17; pp. e202215882 - n/a
• Main Authors: Tang, Jun, He, Jingxi, Zhao, Sheng‐Yin, Liu, Weiping
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 17.04.2023; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Alcohols; Alkylation; Benzyl alcohol; Chemistry; Chemistry, Multidisciplinary; Coupling; Homogeneous Catalysis; Manganese; Methanol; Methylation; Physical Sciences; Science & Technology; Three-Component Coupling; Homogeneous Catalysis; BORROWING HYDROGEN; PYRIMIDINES; IRON; Alcohols; KETONES; REDUCTION; NICKEL; BETA-ALKYLATION; Three-Component Coupling; PINCER COMPLEXES; ESTERS; Methylation; Manganese
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.202215882

Herein, we report a manganese‐catalyzed three‐component coupling of secondary alcohols, primary alcohols and methanol for the synthesis of β,β‐methylated/alkylated secondary alcohols. Using our method, a series of 1‐arylethanol, benzyl alcohol derivatives, and methanol undergo sequential coupling efficiently to construct assembled alcohols with high chemoselectivity in moderate to good yields. Mechanistic studies suggest that the reaction proceeds via methylation of a benzylated secondary alcohol intermediate to generate the final product. For the first time, a manganese‐catalyzed three‐component coupling of secondary alcohol, primary alcohol and methanol for the synthesis of β,β‐methylated/alkylated alcohol with high chemoselectivity is presented.