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Diverse Activation Modes in the Hydroboration of Aldehydes and Ketones with Germanium, Tin, and Lead Lewis Pairs
Author(s) -
Schneider Julia,
Sindlinger Christian P.,
Freitag Sarah M.,
Schubert Hartmut,
Wesemann Lars
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201609155
Subject(s) - hydroboration , chemistry , lewis acids and bases , intramolecular force , tin , catalysis , moiety , reactivity (psychology) , frustrated lewis pair , hydride , reagent , organic chemistry , polymer chemistry , medicinal chemistry , metal , medicine , alternative medicine , pathology
Intramolecular germylene, stannylene, and plumbylene Lewis pairs were reacted with hexanal and yielded the cyclic addition products only with the germanium and tin reagents. In further reactivity studies, the hydroboration of aldehydes and ketones catalyzed by intramolecular germylene, stannylene, and plumbylene Lewis pairs was studied. In the case of the cyclic germylene Lewis pair, the product of the oxidative addition of pinacolborane at the germylene moiety was observed. According to stoichiometric as well as catalytic experiments, the intramolecular germylene Lewis pair acts as a catalyst in the hydroboration of aldehydes and ketones. The homologous stannylene Lewis pair forms a reactive tin hydride during the catalysis, which can also act as a catalyst in this transformation.