Silver-mediated, direct phosphorylation of BODIPY dyes at the 3- or 3,5-positions with H-phosphonates

Abstract

A direct and regioselective C–H/P–H cross-coupling of dialkyl phosphites, and diphenylphosphine oxide to easily available BODIPYs through an Ag-mediated radical addition, resulted in a series of new α-phosphorylated BODIPY fluorophores under mild conditions. Hydrolysis of the phosphonate gave the corresponding BODIPY phosphoric acid, which is soluble and fluorescent in water with a high quantum yield of 0.83.