Aerobic hydroxylation of N-borylenamine: triethylborane-mediated hydroxyalkylation of alpha,beta-unsaturated oxime ether.

Intermolecular hydroxyalkylation of alpha,beta-unsaturated imines involving Et3B-mediated regioselective alkyl radical addition and subsequent hydroxylation with molecular oxygen has been developed, in which N-borylenamine generated by trapping of the enaminyl radical with Et3B was a key intermediate in the proposed aerobic hydroxylation mechanism.