Reduced Phenalenyl in Catalytic Dehalogenative Deuteration and Hydrodehalogenation of Aryl Halides

Dehalogenative deuteration reactions are generally performed through metal-mediated processes. This report demonstrates a mild protocol for hydrodehalogenation and dehalogenative deuteration of aryl/heteroaryl halides (39 examples) using a reduced odd alternant hydrocarbon phenalenyl under transition metal-free conditions and has been employed successfully for the incorporation of deuterium in various biologically active compounds. The combined approach of experimental and theoretical studies revealed a single electron transfer-based mechanism.

Automated summary

This report presents a new method for hydrodehalogenation and dehalogenative deuteration of aryl/heteroaryl halides without the need for transition metals. The incorporation of deuterium into biologically active compounds was successfully achieved, and the mechanism was found to be based on single electron transfer through the combined approach of experimental and theoretical studies.