Publication Date:
2017-07-25
Description:
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 J. Org. Chem. 2017, 13, 1446–1455. doi:10.3762/bjoc.13.142
Keywords:
N-(1-arylalkyl)imidesα-imidoalkylating agentsimidoalkylation reactions1-imidoalkylphosphonium saltsTscherniac–Einhorn-type reaction
Electronic ISSN:
1860-5397
Topics:
Chemistry and Pharmacology
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