The cleavage of a Csp -H bond by an N/B frustrated Lewis pair (FLP) is reported. Upon mild heating, the ambiphilic molecule (2-NMe -C H ) BH activates the C-H bond of a methyl group in α 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.
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