4.7 Article

Cu(II)/PTABS-Promoted, Regioselective SNAr Amination of Polychlorinated Pyrimidines with Mechanistic Understanding

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JOURNAL OF ORGANIC CHEMISTRY
卷 88, 期 15, 页码 11036-11044

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AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.3c01003

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In this study, the highly regioselective nucleophilic aromatic substitution (SNAr) of polychlorinated pyrimidines promoted by Cu(II)/PTABS is reported, aided by DFT predictions of bond dissociation energies. The unique reactivity of Cu(II)-PTABS is attributed to its coordination/activation mechanism, with further insights into the catalytic species provided.
Regioselective amination of polyhalogenated heteroarenes(especiallypyrimidines) has extensive synthetic and commercial relevance fordrug synthesis applications but is plagued by the lack of effectivesynthetic strategies. Herein, we report the Cu(II)/PTABS-promotedhighly regioselective nucleophilic aromatic substitution (SNAr) of polychlorinated pyrimidines assisted by DFT predictions ofthe bond dissociation energies of different C-Cl bonds. Theunique reactivity of Cu(II)-PTABS has been attributed to the coordination/activationmechanism that has been known to operate in these reactions, but furtherinsights into the catalytic species have also been provided.

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