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

• Viktor M. Tkachuk,
• Oleh O. Lukianov,
• Mykhailo V. Vovk,
• Isabelle Gillaizeau and
• Volodymyr A. Sukach

Beilstein J. Org. Chem. 2020, 16, 2304–2313, doi:10.3762/bjoc.16.191

• Enamine LTD, 78 Chervonotkats‘ka str., Kyiv 02094, Ukraine 10.3762/bjoc.16.191 Abstract 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

• products, in contrast to the 4-methyl and 4-unsubstituted substrates which do not undergo N1-arylation under similar reaction conditions. Keywords: C–N cross-coupling; Chan–Evans–Lam reaction; pyrimidin-2(1Н)-ones; fluoroalkyl group; boronic acids; Introduction The catalytic formation of C–N bonds in the

• further the range of reagents, we subjected phenylboronic acid pinacol ester (6а) to a similar model conversion. Boronic acid pinacol esters are generally known to be much less reactive than the corresponding boronic acids in the Chan–Evans–Lam reaction having, on the other hand, the important advantage