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Facile B-H bond activation of borane by stable carbenoid species
Hadrien Heuclin1, Samuel Y-F Ho, Xavier F Le Goff
1Laboratoire Hétéroéléments et Coordination, Ecole Polytechnique, CNRS, Route de Saclay, 91120 Palaiseau, France.
Abstract:
Stable nucleophilic carbene compounds have recently been shown to be able to mimic in some instances the reactivity of metal fragments in the reaction of unactivated E-H bonds (E = H, R3Si, NH2, R2P). However, the insertion into a B-H bond of the strongly Lewis acidic BH3 molecule has never been observed at a single C atom or even at a metal fragment. Our results show that designed stable, highly electrophilic carbenoid fragments in compounds 4 and 6 can achieve this reactivity in a controlled manner. Density functional theory calculations corroborated the experimental results on the presently designed systems as well as the lack of reactivity on nucleophilic carbenes.
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