One-Pot Synthesis of Fluorescent Alkenylated Benzo[a]imidazo[2,1,5-c,d]indolizine via Tandem Intramolecular Direct C–H Bond Arylation Cyclization/Mizoroki–Heck Reaction

Abstract We developed a one-pot synthetic method combining stepwise, direct C–H bond arylation cyclization and the Mizoroki–Heck reaction for the efficient synthesis of benzo[a]imidazo[2,1,5-c,d]indolizine fluorescent cores. This method has a broad substrate scope and applies to both electron-donating and electron-withdrawing styrene derivatives. Evaluation of the photophysical properties revealed that the benzoimidazoindolizine fluorophores synthesized by this method exhibited a red-shift of up to 40 nm in absorption and fluorescence compared to previously reported biaryl-type compounds.