Copper-catalyzed cross-coupling of alkylsamarium reagents with alkyl halides

Abstract SmI 2 /HMPA converts alkyl iodides and bromides to alkyl samarium reagents which can be cross-coupled with primary alkyl iodides and bromides and secondary iodides in the presence of Cu(I) halides or Li 2 CuCl 4 at room temperature. The alkylation of primary iodides gives good yields of cross-coupling products with negligible homo-coupling products. The method is especially useful for the small scale cross-coupling reactions.