C70 as a Photocatalyst for Oxidation of Secondary Benzylamines to Imines

Abstract

Photosensitive C70 was used for the catalytic oxidation of benzylamines to the corresponding imines. The advantages of using C70 compared to C60 or other commonly used photosensitizers such as tetraphenylporphyrin (TPP) are (1) faster reaction rates, especially under lower energy of light sources, (2) clean reactions with simple workup without chromatography, and (3) lower catalyst loadings. The reactions were suitable for various benzylamine derivatives. Subsequent nucleophilic additions to the imines were successfully carried out on substituted products. Quenching experiments in the presence of DABCO and benzoquinone implicate the involvement of the singlet oxygen ((1)O2) and the superoxide radical anion (O2(•-)) as important reactive species in the oxidation.