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Promoting the Hydrosilylation of Benzaldehyde by Using a Dicationic Antimony‐Based Lewis Acid: Evidence for the Double Electrophilic Activation of the Carbonyl Substrate
Authors:Masato Hirai  Junsang Cho  Prof. Dr. François P. Gabbaï
Affiliation:1. Department of Chemistry, Texas A&M University, Texas, USA), Fax;2. http://www.chem.tamu.edu/rgroup/gabbai/+1)?979‐845‐4719
Abstract:The concomitant activation of carbonyl substrates by two Lewis acids has been investigated by using [1,2‐(Ph2MeSb)2C6H4]2+ ([ 1 ]2+), an antimony‐based bidentate Lewis acid obtained by methylation of the corresponding distibine. Unlike the simple stibonium cation [Ph3MeSb]+, dication [ 1 ]2+ efficiently catalyzes the hydrosilylation of benzaldehyde under mild conditions. The catalytic activity of this dication is correlated to its ability to doubly activate the carbonyl functionality of the organic substrate. This view is supported by the isolation of [ 1 ‐μ2‐DMF][OTf]2, an adduct, in which the DMF oxygen atom bridges the two antimony centers.
Keywords:antimony  homogeneous catalysis  cations  hydrosilylation  Lewis acids
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