Scheme 1.1 2 SILVER ALKYLS, ALKENYLS, ARYLS, AND ALKYNYLS IN ORGANIC SYNTHESIS were compared to those for known radically-mediated reactions have suggested that a concerted process is more likely, although this has not proved to be general. [7][8][9] The formation of methylsilver and dimethylargentate has been observed in the collision-induced dissociation MS3 spectrum of silver diacetate. Dimethylargentate is stable in the gas phase, and has been isolated for short periods (10 s) without significant decomposition. 10 Alkylsilver compounds have been prepared by treatment of Grignard reagents with silver salts, [11][12][13][14][15][16][17][18][19] and similarly undergo oxidative homocoupling to give alkyl dimers. [11][12][13]19,20 Exploitation of this finding has resulted in the development of general methodology for silver-catalyzed alkyl-alkyl homocoupling of Grignard reagents (Table 1.1). 21 The catalytic cycle of this reaction is proposed to proceed via the oxidation of metallic silver with 1,2-dibromoethane to generate silver bromide (Scheme 1.2).