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Chan-Evans-Lam N1-(het)arylation and N1-alk?nylation of 4-fluoroalkylpyrimidin-2(1H)-ones.

ABSTRACT: The Chan-Evans-Lam reaction of 1-unsubstituted 4-fluoroalkylpyrimidin-2(1?)-ones with arylboronic acids is reported as a facile synthetic route to hitherto unavailable N1-(het)aryl and N1-alkenyl derivatives of the corresponding pyrimidines. An efficient C-N bond-forming process is also observed by using boronic acid pinacol esters as coupling partners in the presence of Cu(II) acetate and boric acid. The 4-fluoroalkyl group on the pyrimidine ring significantly assists in the formation of the target N1-substituted products, in contrast to the 4-methyl and 4-unsubstituted substrates which do not undergo N1-arylation under similar reaction conditions.

SUBMITTER: Tkachuk VM

PROVIDER: S-EPMC7509380 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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Chan-Evans-Lam N1-(het)arylation and N1-alkеnylation of 4-fluoroalkylpyrimidin-2(1H)-ones.

Tkachuk Viktor M VM Lukianov Oleh O OO Vovk Mykhailo V MV Gillaizeau Isabelle I Sukach Volodymyr A VA

Beilstein journal of organic chemistry 20200917

The Chan-Evans-Lam reaction of 1-unsubstituted 4-fluoroalkylpyrimidin-2(1Н)-ones with arylboronic acids is reported as a facile synthetic route to hitherto unavailable N1-(het)aryl and N1-alkenyl derivatives of the corresponding pyrimidines. An efficient C-N bond-forming process is also observed by using boronic acid pinacol esters as coupling partners in the presence of Cu(II) acetate and boric acid. The 4-fluoroalkyl group on the pyrimidine ring significantly assists in th ...[more]

PMID: 33014170

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