Journal of Organic Chemistry p. 1320 - 1329 (2019)
Update date:2022-08-05
Topics:
Grandane, Aiga
Longwitz, Lars
Roolf, Catrin
Spannenberg, Anke
Escobar, Hugo Murua
Junghanss, Christian
Suna, Edgars
Werner, Thomas
A straightforward two-step synthesis of benzoxepinones was developed via base-free phosphane-catalyzed Wittig reaction. 3-Methyl-1-phenyl-2-phospholene 1-oxide was used as a precatalyst and trimethoxysilane as a reducing agent. Additionally benzoic acid is employed as a catalyst to facilitate the reduction of the phosphane oxide. Mechanistic investigation revealed the formation of a coumarin as a side product, which was identified by 2D NMR experiments. First results of metabolic activity tests on the prepared benzoxepinones are reported.
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