Photo-Ritter Reaction of Arylmethyl Bromides in Acetonitrile

Abstract

The photo-Ritter reaction of five arylmethyl bromides can occur in acetonitrile to give acetamides. The intermediates, carbocations, which are formed from subsequent electron transfer between the radical pairs generated from initial homolytic cleavage of the C–Br bond, are trapped by acetonitrile, and subsequent hydrolysis generates the corresponding acetamides.

Keywords:

• Acetamides
• arylmethyl bromides
• photolysis
• Ritter reaction

ACKNOWLEDGMENT

We thank the National Natural Science Foundation of China (Grant Nos. 20972149 and 30870581).

Notes

^a [Substrate] = 1 mM, determined by high-performance liquid chromatography (HPLC) directly on the crude product mixture.

^b Irradiation wavelengths, which are maxima absorption peaks of arylmethyl bromides.

^c Irradiation time.