Synlett 2000; 2000(6): 0905-0907
DOI: 10.1055/s-2000-6716
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

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.