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Review | Special issue | Vol 30, No. 2, 1990, pp.1155-1193
Published online, 1st January, 1970
DOI: 10.3987/REV-89-SR4
Metallation and Metal-assisted Bond Formation in π-Election Deficient Heterocycles

Kjell Undheim* and Tore Benneche

*Department of Chemistry, University of Oslo, P.O.Box 1033, Blindern, N-0315 Oslo, Norway

Abstract

Regiospecific C-C bond formation in electrophilic positions in π-electron deficient heteroarenes results from 1:1-adduct formation with organometallic reagents and dehydrogenation to heteroarenes. Cross-coupling between halogenoheteroarenes and organostannanes using Pd-catalysis introduces carbon substituents in a regio- or chemoselective manner; a Br- or I-substituent is replaced in any position, a Cl-substituent in an electrophilic position. Methods for the stannylation and palladation of pyrimidines are described. These metallopyrimidines are active in cross-couplong reactions. Pd(0,II)-catalysis has been used in the formation of the C-N bond by rearrangements of 2-propenyloxypyrimidines, and π-allylpalladium complexes in the direct N-alkylation. Preparation and reactions of pyrimidinylcerium dichlorides are discussed.