Hindered organoboron groups in organic chemistry. 24. The condensation of aliphatic aldehydes with dimesitylboron stabilised carbanions to give ketones

Article abstract of DOI:10.1016/S0040-4020(01)87982-5

The condensation of boron stabilised carbanions, MeS₂BCHLiR¹, (R¹≠H) with aliphatic aldehydes, R²CHO, followed by treatment with trifluoroacetic anhydride (TFAA) or N-chlorosuccinimide (NCS) is an unique, broadly applicable redox process that yields ketones, R¹CH₂COR², directly and in high yields. The anion MeS₂BCH₂Li (MeS₂BCHLiR¹, R¹=H) gives high yields of alkenes, R²CH=CH₂ in the same conditions.