Frustrated Lewis Pair Mediated Csp 3 -H Activation.

The cleavage of a Csp(3)-H bond by an N/B frustrated Lewis pair (FLP) is reported. Upon mild heating, the ambiphilic molecule (2-NMe2-C6H4)(2)BH activates the C-H bond of a methyl group in position of a nitrogen atom to generate an unprecedented N-B heterocycle. Upon further heating, the novel species rearranges through a hydride abstraction/1,2-aryl shift sequence. The mechanistic details of these transformations are investigated by quantum mechanical calculations.