TY - JOUR A1 - Tkachuk, Viktor M. A1 - Lukianov, Oleh O. A1 - Vovk, Mykhailo V. A1 - Gillaizeau, Isabelle A1 - Sukach, Volodymyr A. T1 - Chan–Evans–Lam N1-(het)arylation and N1-alkеnylation of 4-fluoroalkylpyrimidin-2(1H)-ones JF - Beilstein Journal of Organic Chemistry PY - 2020/// VL - 16 SP - 2304 EP - 2313 SN - 1860-5397 DO - 10.3762/bjoc.16.191 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.16.191 KW - C–N cross-coupling KW - Chan–Evans–Lam reaction KW - pyrimidin-2(1Н)-ones KW - fluoroalkyl group KW - boronic acids N2 - 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 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. ER -