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Room‐Temperature Guerbet Reaction with Unprecedented Catalytic Efficiency and Enantioselectivity
Author(s) -
Ng Teng Wei,
Liao Gang,
Lau Kai Kiat,
Pan HuiJie,
Zhao Yu
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202004758
Subject(s) - catalysis , chemistry , yield (engineering) , ruthenium , ketone , enantioselective synthesis , alkylation , combinatorial chemistry , primary (astronomy) , redox , organic chemistry , reaction conditions , materials science , physics , astronomy , metallurgy
We report herein an unprecedented highly efficient Guerbet‐type reaction at room temperature (catalytic TON up to >6000). This β‐alkylation of secondary methyl carbinols with primary alcohols has significant advantage of delivering higher‐order secondary alcohols in an economical, redox‐neutral fashion. In addition, the first enantioselective Guerbet reaction has also been achieved using a commercially available chiral ruthenium complex to deliver secondary alcohols with moderate yield and up to 92 % ee . In both reactions, the use of a traceless ketone promoter proved to be beneficial for the catalytic efficiency.