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Catalytic dehydrocoupling of amines and boranes by an incipient tin(ii) hydride
Jeremy D Erickson1, Ting Yi Lai1, David J Liptrot1
1Department of Chemistry, University of California, One Shields Avenue, Davis, California 95616, USA. pppower@ucdavis.edu.
Abstract:
The facile heterodehydrocoupling of a range of primary or secondary amines and even ammonia with pinacolborane (HBPin) was accomplished using {ArMeSn(μ-OMe)}2 (1, ArMe = C6H3-2,6-(C6H2-2,4,6-Me3)2) as pre-catalysts for a catalytically active tin(ii) hydride. The more sterically hindered pre-catalyst 2, {AriPrSn(μ-OMe)}2 (AriPr = C6H3-2,6-(C6H3-2,6-iPr2)2) facilitated the dehydrocoupling only of primary amines with HBPin, and at an increased rate relative to the less crowded {ArMeSn(μ-OMe)}2. Also presented is {ArMeSn(μ-NEt2)}2 (3), which can be converted into the structurally characterizable {ArMeSn(μ-NEt2)(μ-H)SnArMe} (4) via the addition of pinacol borane. This, alongside stoichiometric studies, give insight into the mechanism of the catalysis.
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