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

Diphenyldiazomethane reacts with HB(C 6 F 5 ) 2 and B(C 6 F 5 ) 3 , resulting in 1,1‐hydroboration and adduct formation, respectively. The hydroboration proceeds via a concerted reaction involving initial formation of the Lewis adduct Ph 2 CN 2 BH(C 6 F 5 ) 2 . The highly sensitive adduct Ph 2 CN 2 (B(C 6 F 5 ) 3 ) liberates N 2 and generates Ph 2 CB(C 6 F 5 ) 3 . DFT computations reveal that formation of Ph 2 CN 2 B(C 6 F 5 ) 3 from carbene, N 2 , and borane is thermodynamically favourable, suggesting steric frustration could preclude carbene–borane adduct formation and affect FLP‐N 2 capture.