The Coupling of Organic Radicals by the Action of Grignard Reagents on Heavy Metal Salts. II. Coupling of Dissimilar Radicals

The Action of Grignard Reagents on Heavy Metal Salts. Iii. Mixed Grignard Reagents and Silver Bromide

“…The action of silver bromide on a number of pairs of Grignard reagents has been studied. 2. It has been found that there is a definite relation between the course of the reaction and the relative electronegativities of the radicals involved.…”

Silver Alkyls, Alkenyls, Aryls, and Alkynyls in Organic Synthesis

“…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).…”