Jm. Khurana et A. Ray, CHEMOSELECTIVE REDUCTIVE COUPLING OF NITROARENES WITH MAGNESIUM IN METHANOL VIA SINGLE-ELECTRON TRANSFER, Bulletin of the Chemical Society of Japan, 69(2), 1996, pp. 407-410
A chemoselective reductive coupling of nitroarenes using magnesium in
methanol has been reported at ambient temperature. While the cyano, fo
rmyl, methoxycarbonyl, methyl, methoxy, phenyl, amino, and chloro grou
ps are unaffected, iodo and bromo groups undergo dehalogenation but in
a slower reaction than the coupling of nitro group. The coupling is b
elieved to be proceeding via SET from Mg to nitroarenes.