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A meso BODIPY-type photoremovable protecting group for carboxyl group is developed. BODIPYs are well-known for brilliant color, favorable to reaction monitor and purification. meso-BODIPY esters are achieved via esterification in yield of 44~89%, while deprotection is fulfilled under irradiation of blue LED bulb in the presence of photocatalyst and organic hydrogen donor in yield of 43~95%. This method is applicable to a variety of acids, such as aromatic, heteroaromatic, alkyl, α,β-unsaturated carboxylic acids et al. Our BODIPY-deprotective condition is almost neutral that both methylate and tert-butylate are compatible.
Yang et al. (Thu,) studied this question.