This article deals with our recent results on the investigation of the
reaction and synthetic application of trialkyl 2-indolylborate. (1)Hi
gh regioselectivity on the reaction of the indolylborate with electrop
hiles in the presence of copper(I) ion, highly depending on the nature
of electrophiles used, was found. (2)Synthetic application of an intr
amolecular alkyl migration process in the indolylborate for the constr
uction of cyclo[1,2-a]and cyclo[1,2-b]indole systems was realized vie
an intramolecular cyclization process. (3)Palladium catalyzed cross co
upling, carbonylative cross coupling and tandem cyclization cross coup
ling reactions with the indolylborate were developed and used for the
preparation of indole derivatives.