Beilstein J. Org. Chem.2020,16, 3086–3092, doi:10.3762/bjoc.16.258
stereoselective manner under mild reaction conditions. This reaction is operationally simple and offers an excellent functional group tolerance as well as a broad substrate scope that includes both terminal and internal alkynes. The reaction proceeded through the oxidative generation of a P-centeredradical and
subsequent fluorine atom transfer.
Keywords: β-fluorovinylphosphonates; fluorine atom transfer; P-centeredradical; silver catalysis; three-component reaction; Introduction
As one of the most important topics in organic chemistry, the introduction of fluorine and phosphorus atoms into double bonds is an
selectflour to generate Ag(III)F. Subsequently, ethyl phosphite is oxidized by Ag(III)F to generate a P-centeredradical (INT-I) and Ag(II)F. The electrophilic phosphonyl radical addition to the triple bond of 1a generates the vinyl-free radical INT-II, which is subsequently trapped by AgF(II) to afford the
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Graphical Abstract
Scheme 1:
Metal-catalyzed difunctionalization of unsaturated carbon–carbon bonds.