TBHP/Et 3 N-Promoted Chemoselective Formylation and Peroxidation of Pyrrolo[2,1- a ]isoquinolines.

An efficient formylation of pyrrolo[2,1- a ]isoquinoline derivatives has been reached by the use of TBHP ( t BuOOH) and Et 3 N as the mediator. In this strategy, CHO and CDO can be readily incorporated into heteroarenes by the utilization of CHCl 3 and CDCl 3 as the carbonyl sources. Interestingly, a solvent-controlled chemoselectivity was observed. The use of PhCl as a solvent resulted in dearomatization and peroxidation of pyrrolo[2,1- a ]isoquinolines, delivering functionalized peroxides in 53-64% yields.