THE EFFECTIVENESS OF COPPER(I) COMPOUNDS AS CATALYSTS IN THE COUPLING OF PHENYLLITHIUM WITH PRIMARY ALKYL-HALIDES AND TOSYLATES


ERDIK E., DASKAPAN T.

SYNTHESIS AND REACTIVITY IN INORGANIC AND METAL-ORGANIC CHEMISTRY, cilt.25, sa.9, ss.1517-1527, 1995 (SCI-Expanded) identifier identifier

Özet

Various uncomplexed and complexed Cu(I) salts, Li2CuCl4, Li2CuCl3, Ph(2)CuLi and PhCu, have been tested as catalysts in the coupling reactions of phenyllithium with 2-chloroethanol, ethyl bromide, 2-chloroethyl tosylate and ethyl tosylate. CuBr.Me(2)S, CuCN, CuI.PBu(3)-(n) under bar and CuI have been found to be the most effective and selective catalysts in diethyl ether, respectively, for these couplings. The catalytic activity in Cu(I) catalyzed coupling reactions of phenyllithium depends on the reaction conditions, on the nucleofugal group, and on the 2-heteroatom functionality of the substrate.