Dibromo-BODIPY as an Organic Photocatalyst for Radical-Ionic Sequences

A new dibrominated 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) is reported as a new metal-free photocatalyst. This BODIPY showed similar optoelectronic, electrochemical, and performance properties to those of Ru(bpy)(3)Cl-2, one of the most common photocatalysts in a known radical-ionic transformation, such as the formation of 1,4-dicarbonyl compounds. Moreover, additional sequences in which the generated oxonium ion is trapped by an internal nucleophile were developed using this BODIPY photocatalyst. These new sequences allowed the straightforward preparation of gamma-alkoxylactones, monoprotected 1,4-ketoaldehydes, and dihydrofurans. This new catalyst, the methodology, and the forged functional groups could be important tools in organic synthesis.

Automated summary

A new metal-free photocatalyst, dibrominated BODIPY, has been reported with similar properties to the common photocatalyst Ru(bpy)(3)Cl-2. This catalyst can be used to develop new reaction sequences in organic synthesis, showing potential in the formation of various compounds.