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Synlett 2000; 2000(6): 0905-0907
DOI: 10.1055/s-2000-6716
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Palladium-Catalyzed Cross-Coupling of Benzylzinc Reagents with Methylthio N-Heterocycles: A New Coupling Reaction with Unusual Selectivity

Mary E. Angiolelli* , Albert L. Casalnuovo, Thomas P. Selby
  • *DuPont Agricultural Products, Stine-Haskell Research Center, Newark, Delaware 19714, USA
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Publication Date:
31 December 2000 (online)

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Benzylzinc reagents undergo palladium-catalyzed cross-coupling reactions with methylthio-substituted N-heterocycles in moderate to good yields. 2-(Methylthio)pyrimidines are particularly reactive substrates for this reaction. As a result, the regioselectivity of 2,4-bis(methylthio)pyrimidines is opposite to that of their 2,4-dichloropyrimidine analogues. This unusual cross-coupling reaction offers new flexibility in the regioselective synthesis of substituted pyrimidines and other heterocycles.

cross-coupling - benzylzinc reagents - thioethers - heterocycles - regioselectivity