ArticleSynlett : accounts and rapid communications in synthetic organic chemistry2025
Inverting the Conventional Site Selectivity of Cross-Coupling of 2,4-Dichloropyrimidines.
Article in Synlett : accounts and rapid communications in synthetic organic chemistry, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
Cross-coupling and nucleophilic aromatic substitution reactions of 2,4-dihalopyrimidines generally favor reaction at the C4 site, especially in the absence of other substituents on the pyrimidine ring. Here we review our recent discovery of reaction conditions that enable C2-selective Pd-catalyzed C-S coupling of unsubstituted 2,4-dichloropyrimidines, as well as some substituted derivatives. The unusual C2-selectivity complements previously established cross-coupling methods and raises interesting mechanistic questions about oxidative addition in cross-coupling catalytic cycles.
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