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C‐Alkylation of Secondary Alcohols by Primary Alcohols through Manganese‐Catalyzed Double Hydrogen Autotransfer
Author(s) -
ElSepelgy Osama,
Matador Esteban,
Brzozowska Aleksandra,
Rueping Magnus
Publication year - 2019
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201801660
Subject(s) - alkylation , chemistry , catalysis , manganese , primary (astronomy) , ligand (biochemistry) , halide , alkyl , organic chemistry , pincer ligand , hydrogen , alcohol , combinatorial chemistry , noble metal , pincer movement , biochemistry , physics , receptor , astronomy
A new Mn‐catalyzed alkylation of secondary alcohols with non‐activated alcohols is presented. The use of a stable and well‐defined manganese pincer complex, stabilized by a PNN ligand, together with a catalytic amount of base enabled the conversion of renewable alcohol feedstocks to a broad range of higher‐value alcohols in good yields with water as the sole byproduct. The strategy eliminates the need for exogenous and detrimental alkyl halides as well as the use of noble metal catalysts, making the C‐alkylation through double hydrogen autotransfer a highly sustainable and environmentally benign process. Mechanistic investigations support a hydrogen autotransfer mechanism in which a non‐innocent ligand plays a crucial role.