Beilstein J. Org. Chem.2017,13, 1446–1455, doi:10.3762/bjoc.13.142
Gliwice, Poland Department of Chemical Organic Technology and Petrochemistry, Silesian University of Technology, B. Krzywoustego 4, 44-100 Gliwice, Poland 10.3762/bjoc.13.142 Abstract An effective synthesis of the hitherto unknown 1-imidoalkylphosphoniumsalts has been developed in the reported study
triarylphosphonium tetrafluoroborate. The imidoalkylating properties of the obtained 1-imidoalkylphosphoniumsalts were tested using the Tscherniac–Einhorn-type reaction with aromatic hydrocarbons as a model reaction. It was found that the Cα–P+ bond strength can be considerably reduced and the imidoalkylation of
arenes can be markedly facilitated using 1-imidoalkylphosphoniumsalts derived from triarylphosphines with electron-withdrawing substituents such as tris(m-chorophenyl)phosphine, tris(p-chlorophenyl)phosphine and tris[p-(trifluoromethyl)phenyl]phosphine. Microwave irradiation also considerably
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Graphical Abstract
Scheme 1:
α-Amidoalkylation reactions under basic or acidic conditions.