The group publishes a Lewis Base Promoted Selective C-N Borylation of Alkyl Amines on Angew. Congrats Hu!

ABSTRACT: An efficient method for metal-free deaminative borylation of alkylamines using bis-(catecholato)diboron as the boron source to directly synthesize various alkyl potassium trifluoroborate salts is introduced. The key to this high reactivity is the utilization of pyridinium salt-activated alkylamines, with a catalytic amount of a bipyridine-type Lewis base as a promoter. This transformation shows good functional group compatibility (e.g., being unimpeded by the presence of a ketone, indole, internal alkene, or unactivated alkyl chloride) and can serve as a powerful synthetic tool for borylation of amine groups in complex compounds. Mechanistic experiments and computations suggest a mechanism in which the Lewis-base activated B2cat2 unit intercepts an alkyl radical generated by single-electron transfer (SET) from a boron-based reductant