In combination with Na metal at room temperature in benzene, cyano groups are cleaved from alkyl nitriles to give the corresponding hydrocarbons: J. Am. Chem. Soc., 93, 7113 (1971). Catalyst for the coupling of Grignard reagents with aryl halides: J. Am. Chem. Soc., 124, 13856 (2002); Org. Lett., 6, 1227 (2004), with vinyl sulfones to give alkenes: Tetrahedron Lett., 23, 2469 (1982); Tetrahedron, 44, 111 (1988), and with acyl halides to give ketones in good yield: Tetrahedron Lett., 25, 4805 (1984). Alkenyl halides couple with aryl Grignards to give 1-aryl alkenes: Synlett, 1901 (2001). For leading references and improved reaction conditions for the coupling of alkyl and aryl Grignards with a varirtety of enol triflates and acid chlorides, and also for selective monoalkylation of dichlroarenes and heteroarenes, see: J. Org. Chem., 69, 3743 (2004).Catalyzes the nitration of non-activated arenes, e.g. halogenobenzenes, and moderately activated arenes, e.g. alkylbenzenes and naphthalenes under non-acidic, non-aqueous conditions with NO2 in the presence of O2; no nitration occurs in the absence of the Fe(III) catalyst: J. Chem. Soc., Perkin 1, 2385 (1996).
