COPPER CYANIDE-CATALYZED PALLADIUM COUPLING OF N-TERT-BUTOXYCARBONYL-PROTECTED ALPHA-LITHIO AMINES WITH ARYL IODIDES OR VINYL IODIDES

Treatment of (alpha-aminoalkyl)lithium reagents with aryl iodides in t he presence of catalytic amounts of CuCN and PdCl2(PPh3)(2) or [(p-MeO C6H4)(3)P](4)Pd affords 2-aryl substituted amines in modest to good yi elds. The yields can be improved by use of softer ligands such as AsPh 3 and SbPh3 or by use of bis(diphenylphosphino)ferrocene (dppf). Coupl ed products are obtained with electron-rich aryl iodides (XArI, X = Me , OMe), and the reaction fails with electron-poor aryl iodides (XArI, X = NO2, CO2Li). Treatment of the (alpha-aminoalkyl)lithium reagents w ith vinyl iodides and Pd(0)/dppf/CuCN afforded the coupling products i n low to modest yields.