Intramolecular Base-Free Catalytic Wittig Reaction: Synthesis
of Benzoxepinones
Version 2 2019-02-14, 12:48
Version 1 2019-01-22, 12:34
Posted on 2019-02-14 - 12:48
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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Grandane, Aiga; Longwitz, Lars; Roolf, Catrin; Spannenberg, Anke; Murua Escobar, Hugo; Junghanss, Christian; et al. (2019). Intramolecular Base-Free Catalytic Wittig Reaction: Synthesis
of Benzoxepinones. ACS Publications. Collection. https://doi.org/10.1021/acs.joc.8b02789
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AUTHORS (8)
AG
Aiga Grandane
LL
Lars Longwitz
CR
Catrin Roolf
AS
Anke Spannenberg
HM
Hugo Murua Escobar
CJ
Christian Junghanss
ES
Edgars Suna
TW
Thomas Werner
KEYWORDS
2 D NMR experimentsagentMechanistic investigationIntramolecular Base-Free Catalytic Wittig Reactioncoumarinprecatalystactivity testsBenzoxepinonesynthesisphosphane oxideFirst resultsbenzoic acidtrimethoxysilaneformation3- Methyl -1-phenyl 1- oxidebenzoxepinonebase-free phosphane-catalyzed Wittig reactionside productSynthesicatalyst