Palladium-catalyzed Negishi cross-coupling reactions of unactivated alkyl iodides, bromides, chlorides, and tosylates

A single method (2% Pd-2(dba)(3)/8% PCyp(3)/NMI in THF/NMP at 80 degreesC; Cyp = cyclopentyl) achieves the cross-coupling of a range of beta-hydrogen-containing primary alkyl iodides, bromides, chlorides, and tosylates with an array of alkyl-, alkenyl-, and arylzinc halides. The process is compatible with a variety of functional groups, including esters, amides, imides, nitriles, and heterocycles.