Base-promoted, deborylative secondary alkylation of N-heteroaromatic N-oxides with internal gem-bis[(pinacolato)boryl]alkanes: a facile derivatization of 2,2′-bipyridyl analogues

A base-promoted, secondary alkylation of N-heteroaromatic N-oxides using internal gem-bis[(pinacolato)boryl]alkanes as alkylation reagents is reported. The reaction exhibits a broad scope, providing deoxygenated secondary alkylated N-heteroaromatic compounds with high efficiency. The usefulness of the developed protocol is evidenced by the sequential direct alkylation of 2,2'-bipyridine-N-oxide.