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Updated: Apr 23, 2026
08:46
Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
Published on: November 22, 2016
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Developing phospha-Stork chemistry induced by a borane Lewis acid
Yasuharu Hasegawa1, Constantin G Daniliuc, Gerald Kehr
1Organisch-Chemisches Institut der Universität Münster, Correnstrasse 40, 48149 Münster (Germany).
Angewandte Chemie (International Ed. in English)
|September 23, 2014
Summary
Bulky vinyl phosphanes react with aryl aldehydes and enones using a Lewis acid catalyst to form new carbon-carbon bonds, yielding phosphonium salts and cyclobutane products.
Area of Science:
- Organophosphorus Chemistry
- Catalysis
- Organic Synthesis
Background:
- Vinyl phosphanes are versatile building blocks in organic synthesis.
- Lewis acid catalysis offers efficient pathways for C-C bond formation.
- The development of novel synthetic methodologies for complex molecule construction is crucial.
Purpose of the Study:
- To explore the reactivity of bulky vinyl phosphanes in Lewis acid-catalyzed reactions.
- To develop new methods for synthesizing methylene phosphonium salts and cyclobutane derivatives.
- To investigate the scope and limitations of these transformations.
Main Methods:
- Reactions of dimesityl(vinyl)phosphane with aryl aldehydes catalyzed by B(C6F5)3.
- Phospha-Stork reaction of dimesityl(vinyl)phosphane with bulky enones catalyzed by B(C6F5)3.
- Isolation and characterization of the resulting products.
Main Results:
- Bulky vinyl phosphanes successfully undergo carbon-carbon coupling with aryl aldehydes.
- Isolable methylene phosphonium products were obtained from the reaction with aldehydes.
- Efficient synthesis of substituted cyclobutane products via phospha-Stork reaction with enones was achieved.
Conclusions:
- The Lewis acid B(C6F5)3 effectively catalyzes reactions of bulky vinyl phosphanes.
- New synthetic routes to valuable organophosphorus compounds and cyclic structures have been established.
- These methods provide access to complex molecules with potential applications in various fields.
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