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. 2011:7:1648-55.
doi: 10.3762/bjoc.7.194. Epub 2011 Dec 8.

The application of a monolithic triphenylphosphine reagent for conducting Appel reactions in flow microreactors

Kimberley A Roper  1 , Heiko Lange, Anastasios Polyzos, Malcolm B Berry, Ian R Baxendale, Steven V Ley
Affiliations

The application of a monolithic triphenylphosphine reagent for conducting Appel reactions in flow microreactors

Kimberley A Roper et al. Beilstein J Org Chem. 2011.

Abstract

Herein we describe the application of a monolithic triphenylphosphine reagent to the Appel reaction in flow-chemistry processing, to generate various brominated products with high purity and in excellent yields, and with no requirement for further off-line purification.

Keywords: Appel reaction; bromination; flow chemistry; solid-supported reagent; triphenylphosphine monolith.

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Figures

Scheme 1
Scheme 1
The two proposed mechanistic pathways for the Appel reaction.
Scheme 2
Scheme 2
Functionalisation of the triphenylphosphine monolith by using carbon tetrabromide in a recycling process.
Figure 1
Figure 1
a. Unfunctionalised triphenylphosphine monolith; b. Monolith after fuctionalisation with carbon tetrabromide; c. Monolith after partial consumption of the active brominating agent.
Scheme 3
Scheme 3
Flow synthesis of bromides from alcohols by using the functionalised triphenylphosphine monolith.
Figure 2
Figure 2
Linear decrease of the brown decolourisation.
See this image and copyright information in PMC

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