{uni_hamburg} Short: II/25D

{ALF} Catalyst for a variety of coupling reactions, e.g.: Coupling of Grignard reagents to give biaryls: J. Org. Chem., 41, 2252 (1976). Coupling of Grignards with silyl enol ethers of both aldehydes and ketones, to give alkenes. In contrast to Dichlorobis(triphenyl­phosphine)­nickel(II)­, 13930, this reagent gives the thermodynamically more stable alkene: Tetrahedron Lett., 3915 (1980). Cross-coupling of alkyl iodides with dialkylzinc reagents tolerates a variety of functionalities: Angew. Chem. Int. Ed., 34, 2723 (1995).

{ALD} Merck: 14,6500

Beilstein: 1,IV,3677

{ALF} Aryl phosphates couple with Grignards (aryl tosylates do not couple under these conditions), affording high yields of biaryls: Tetrahedron Lett., 22, 4449 (1981). Cross-coupling of aryl chlorides with arylzincs also yields biaryls: Tetrahedron Lett., 39, 6441, 7275 (1998).

{ALD} Merck: 14,6500

{ALF} For a brief feature on uses of the reagent in synthesis, see: Synlett, 1042 (2005).

{ALF} For use in the condensation of active methylene compounds with lactims, see Isopropyl­idene malonate, A15603.

{ALF} Catalyst for the conjugate addition of 1,3-dicarbonyl compounds to various Michael acceptors: J. Org. Chem., 45, 1246 (1980).