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

• Jakub Adamek,
• Roman Mazurkiewicz,
• Anna Węgrzyk and
• Karol Erfurt

Beilstein J. Org. Chem. 2017, 13, 1446–1455, doi:10.3762/bjoc.13.142

• facilitates the cleavage of the highly polar Cα–P+ bond. Keywords: N-(1-arylalkyl)imides; α-imidoalkylating agents; imidoalkylation reactions; 1-imidoalkylphosphonium salts; Tscherniac–Einhorn-type reaction; Introduction The aminomethylation of C–H acidic compounds by the condensation of non-enolizable

• -imidoalkylphosphonium salts 5 applied in the Tscherniac–Einhorn-type reaction with aromatic hydrocarbons as a model reaction. The obtained N-(1-arylalkyl)imides can easily be transformed to the corresponding primary 1-arylalkylamines, following the well-known procedures developed for the Gabriel synthesis of primary

• pressure. Transformation of 1-(N-imido)alkyltriarylphosphonium salts 5 to N-(1-arylalkyl)imides 9; general procedure: A suspension of 1-(N-imido)alkyltriarylphosphonium salt 5 (0.1 mmol) in an aromatic compound (1 cm3) was placed in a glass vial sealed with a screw-cap. To improve the solubility of the