Issue 94, 2016

Catalytic dehydrocoupling of amines and boranes by an incipient tin(ii) hydride

Abstract

The facile heterodehydrocoupling of a range of primary or secondary amines and even ammonia with pinacolborane (HBPin) was accomplished using {ArMe6Sn(μ-OMe)}2 (1, ArMe6 = 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, {AriPr4Sn(μ-OMe)}2 (AriPr4 = 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 {ArMe6Sn(μ-OMe)}2. Also presented is {ArMe6Sn(μ-NEt2)}2 (3), which can be converted into the structurally characterizable {ArMe6Sn(μ-NEt2)(μ-H)SnArMe6} (4) via the addition of pinacol borane. This, alongside stoichiometric studies, give insight into the mechanism of the catalysis.

Graphical abstract: Catalytic dehydrocoupling of amines and boranes by an incipient tin(ii) hydride

Supplementary files

Article information

Article type
Communication
Submitted
24 Aug. 2016
Accepted
22 Sept. 2016
First published
22 Sept. 2016

Chem. Commun., 2016,52, 13656-13659

Catalytic dehydrocoupling of amines and boranes by an incipient tin(II) hydride

J. D. Erickson, T. Y. Lai, D. J. Liptrot, M. M. Olmstead and P. P. Power, Chem. Commun., 2016, 52, 13656 DOI: 10.1039/C6CC06963K

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