The first radical-type selenium(II)–nitrogen exchange (SeNEx) chemistry was successfully developed, enabling rapid synthesis of diaryl selenides in moderate to excellent yields (46 examples, 21–89%). This chemistry brings arylhydrazines into the SeNEx platform and features mild and robust conditions, scalability, air and water tolerance, broad substrate scope, and good atomic economy, with N2 and H2O as the only waste. Furthermore, it tolerates a broad scope of transformable handles such as −OH, −NHBoc, nitro, phenol, ester, amide, sulfonamide, and N-unprotected heterocycles. The results of a mechanistic study support the radical pathway of this reaction. The utilization of this chemistry has been demonstrated by the further −OH- and −NHBoc-based elaboration, highlighting the great potential of this SeNEx chemistry in the synthesis of advanced selenide compounds with drug-like properties.
Pang et al. (Wed,) studied this question.