(<i>E</i>)-9-(2-Iodovinyl)-9<i>H</i>-carbazole: A New Coupling Reagent for the Synthesis of π-Conjugated Carbazoles

Abstract

The one-pot synthesis of (E)-9-(2-iodovinyl)-9H-carbazole via sequential ruthenium-catalyzed silylative coupling of N-vinylcarbazole with vinyltrimethylsilane and iododesilylation is reported. Its use as a new building block in the palladium-catalyzed Sonogashira and Suzuki-Miyaura coupling reactions to yield new carbazole-containing (E)-but-1-en-3-ynes and (E,E)-buta-1,3-dienes is demonstrated.