ChemInform Abstract: Catalytic Effect of a BH3:N,N-Diethylaniline Complex in the Formation of Alkenyl Catecholboranes from Alk-1-ynes and Catecholborane.

ChemInform Abstract

Catecholborane (I), prepared from catechol and diborane in benzene, undergoes coupling reaction with the terminal alkynes (II) in the presence of the N,N-diethylaniline-borane complex, yielding the vinylated catecholboranes (III). These are oxidatively cleaved with hydrogen peroxide to produce the aldehydes (IV). Hydrolysis of (III) gives the boronic acids (V) which are deboronated upon treatment with iodine, forming the trans-iodoalkenes (VI).