Organoboranes. 41. Reaction of Organoboranes with (Dichloromethyl)lithium. Scope and Limitations. Synthesis of Homologated Primary and Secondary Alcohols

Article abstract of DOI:10.1021/jo00221a014

Homologated primary alcohols were prepared from alkylboronic esters by the reaction with (dichloromethyl)lithium, LiCHCl2, followed by KIPBH treatment and oxidation.Homologated secondary alcohols were prepared from representative dialkylborinic esters and trialkylboranes by the reaction with LiCHCl2, followed by treatment with base and oxidation.The yields are generally good with both boronic and borinic esters.On the other hand, the reactions with trialkylboranes exhibited a sensitivity to large steric requirements in the trialkylborane reactant.