1,1-Hydroboration and a Borane Adduct of Diphenyldiazomethane: A Potential Prelude to FLP-N 2 Chemistry

Diphenyldiazomethane reacts with HB(C F ) and B(C F ) , resulting in 1,1-hydroboration and adduct formation, respectively. The hydroboration proceeds via a concerted reaction involving initial formation of the Lewis adduct Ph CN BH(C F ) . The highly sensitive adduct Ph CN (B(C F ) ) liberates N and generates Ph CB(C F ) . DFT computations reveal that formation of Ph CN B(C F ) from carbene, N , and borane is thermodynamically favourable, suggesting steric frustration could preclude carbene-borane adduct formation and affect FLP-N capture.