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Catalytic dehydrocoupling of amines and boranes by an incipient tin(<scp>ii</scp>) hydride
35
Citations
33
References
2016
Year
The facile heterodehydrocoupling of a range of primary or secondary amines and even ammonia with pinacolborane (HBPin) was accomplished using {Ar<sup>Me<sub>6</sub></sup>Sn(μ-OMe)}<sub>2</sub> (1, Ar<sup>Me<sub>6</sub></sup> = C<sub>6</sub>H<sub>3</sub>-2,6-(C<sub>6</sub>H<sub>2</sub>-2,4,6-Me<sub>3</sub>)<sub>2</sub>) as pre-catalysts for a catalytically active tin(ii) hydride. The more sterically hindered pre-catalyst 2, {Ar<sup>iPr<sub>4</sub></sup>Sn(μ-OMe)}<sub>2</sub> (Ar<sup>iPr<sub>4</sub></sup> = C<sub>6</sub>H<sub>3</sub>-2,6-(C<sub>6</sub>H<sub>3</sub>-2,6-iPr<sub>2</sub>)<sub>2</sub>) facilitated the dehydrocoupling only of primary amines with HBPin, and at an increased rate relative to the less crowded {Ar<sup>Me<sub>6</sub></sup>Sn(μ-OMe)}<sub>2</sub>. Also presented is {Ar<sup>Me<sub>6</sub></sup>Sn(μ-NEt<sub>2</sub>)}<sub>2</sub> (3), which can be converted into the structurally characterizable {Ar<sup>Me<sub>6</sub></sup>Sn(μ-NEt<sub>2</sub>)(μ-H)SnAr<sup>Me<sub>6</sub></sup>} (4) via the addition of pinacol borane. This, alongside stoichiometric studies, give insight into the mechanism of the catalysis.
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