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Acid–Base Pairs in Lewis Acidic Zeolites Promote Direct Aldol Reactions by Soft Enolization
Author(s) -
Lewis Jennifer D.,
Van de Vyver Stijn,
RománLeshkov Yuriy
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201502939
Subject(s) - lewis acids and bases , keto–enol tautomerism , chemistry , aldol condensation , aldol reaction , catalysis , base (topology) , acetone , organic chemistry , proton , medicinal chemistry , mathematics , physics , quantum mechanics , mathematical analysis
Hf‐, Sn‐, and Zr‐Beta zeolites catalyze the cross‐aldol condensation of aromatic aldehydes with acetone under mild reaction conditions with near quantitative yields. NMR studies with isotopically labeled molecules confirm that acid‐base pairs in the Si‐O‐M framework ensemble promote soft enolization through α‐proton abstraction. The Lewis acidic zeolites maintain activity in the presence of water and, unlike traditional base catalysts, in acidic solutions.