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Scope and Mechanisms of Frustrated Lewis Pair Catalyzed Hydrogenation Reactions of Electron‐Deficient CC Double Bonds
Author(s) -
Morozova Varvara,
Mayer Peter,
Berionni Guillaume
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201507298
Subject(s) - phosphonium , frustrated lewis pair , iminium , chemistry , nucleophile , lewis acids and bases , hydride , catalysis , triethylsilane , electrophile , medicinal chemistry , double bond , photochemistry , organic chemistry , hydrogen
Several phosphonium and ammonium triarylborohydrides, which are intermediates in hydrogenation reactions catalyzed by frustrated Lewis pairs, were synthesized in high yield under mild conditions from triaryl boranes, ammonium or phosphonium halides, and triethylsilane. The kinetics and mechanisms of the reactions of these hydridoborate salts with benzhydrylium ions, iminium ions, quinone methides, and Michael acceptors were investigated, and their nucleophilicity was determined and compared with that of other hydride donors.