The generation of 2-indolylacyl radicals from the corresponding phenyl sele
noesters, aldehydes, and cr keto carboxylic acids and the scope of their pa
rticipation in intermolecular addition reactions to carbon-carbon double bo
nds have been studied. Whereas the phenyl selenoester method has provided e
asy access to a variety of 1,4-dicarbonyl compounds bearing the 2-acylindol
e moiety, the glyoxylic acid route has been employed for the preparation of
2-indolyl pyridyl ketones.