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An effective synthesis of the hitherto unknown 1-imidoalkylphosphonium salts has been developed in the reported study. The crucial step in the method included the decarboxylative α-methoxylation of N -phthaloyl- or N -succinylamino acids to the corresponding N -(1-methoxyalkyl)imides, followed by the displacement of the methoxy group by the triarylphosphonium group through melting of the imide derivative with triarylphosphonium tetrafluoroborate. The imidoalkylating properties of the obtained 1-imidoalkylphosphonium salts were tested using the Tscherniac-Einhorn-type reaction with aromatic hydrocarbons as a model reaction. It was found that the C α -P + bond strength can be considerably reduced and the imidoalkylation of arenes can be markedly facilitated using 1-imidoalkylphosphonium salts 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 facilitates the cleavage of the highly polar C α -P + bond.

beilstein journal of organic chemistry

1-Imidoalkylphosphonium salts with modulated C<sub>α</sub>–P<sup>+</sup> bond strength: synthesis and application as new active α-imidoalkylating agents

1-Imidoalkylphosphonium salts with modulated Cα–P+ bond strength: synthesis and application as new active α-imidoalkylating agents

1-Imidoalkylphosphonium salts with modulated C_α–P⁺ bond strength: synthesis and application as new active α-imidoalkylating agents