The application of a monolithic triphenylphosphine reagent for conducting Ramirez gem-dibromoolefination reactions in flow

The application of a monolithic form of triphenylphosphine to the Ramirez gem-dibromoolefination reaction using flow chemistry techniques is reported. A variety of gem-dibromides were synthesised in high purity and excellent yield following only removal of solvent and no further off-line purificatio...

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Main Authors: Kimberley A. Roper, Malcolm B. Berry, Steven V. Ley
Format: Article
Language:English
Published: Beilstein-Institut 2013-09-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
Online Access:https://doi.org/10.3762/bjoc.9.207
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author Kimberley A. Roper
Malcolm B. Berry
Steven V. Ley
author_facet Kimberley A. Roper
Malcolm B. Berry
Steven V. Ley
author_sort Kimberley A. Roper
collection DOAJ
description The application of a monolithic form of triphenylphosphine to the Ramirez gem-dibromoolefination reaction using flow chemistry techniques is reported. A variety of gem-dibromides were synthesised in high purity and excellent yield following only removal of solvent and no further off-line purification. It is also possible to perform the Appel reaction using the same monolith and the relationship between the mechanisms of the two reactions is discussed.
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spelling doaj.art-f8f1382dbafe45aa8dffdb56e8f0261d2022-12-21T23:38:22ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972013-09-01911781179010.3762/bjoc.9.2071860-5397-9-207The application of a monolithic triphenylphosphine reagent for conducting Ramirez gem-dibromoolefination reactions in flowKimberley A. Roper0Malcolm B. Berry1Steven V. Ley2Innovative Technology Centre, Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, Cambridgeshire, CB2 1EW, U.K.GlaxoSmithKline, Gunnels Wood Road, Stevenage, Hertfordshire, SG1 2NY, U.K.Innovative Technology Centre, Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, Cambridgeshire, CB2 1EW, U.K.The application of a monolithic form of triphenylphosphine to the Ramirez gem-dibromoolefination reaction using flow chemistry techniques is reported. A variety of gem-dibromides were synthesised in high purity and excellent yield following only removal of solvent and no further off-line purification. It is also possible to perform the Appel reaction using the same monolith and the relationship between the mechanisms of the two reactions is discussed.https://doi.org/10.3762/bjoc.9.207brominationflow chemistryRamirez gem-dibromoolefination reactionsolid-supported reagenttriphenylphosphine monolith
spellingShingle Kimberley A. Roper
Malcolm B. Berry
Steven V. Ley
The application of a monolithic triphenylphosphine reagent for conducting Ramirez gem-dibromoolefination reactions in flow
Beilstein Journal of Organic Chemistry
bromination
flow chemistry
Ramirez gem-dibromoolefination reaction
solid-supported reagent
triphenylphosphine monolith
title The application of a monolithic triphenylphosphine reagent for conducting Ramirez gem-dibromoolefination reactions in flow
title_full The application of a monolithic triphenylphosphine reagent for conducting Ramirez gem-dibromoolefination reactions in flow
title_fullStr The application of a monolithic triphenylphosphine reagent for conducting Ramirez gem-dibromoolefination reactions in flow
title_full_unstemmed The application of a monolithic triphenylphosphine reagent for conducting Ramirez gem-dibromoolefination reactions in flow
title_short The application of a monolithic triphenylphosphine reagent for conducting Ramirez gem-dibromoolefination reactions in flow
title_sort application of a monolithic triphenylphosphine reagent for conducting ramirez gem dibromoolefination reactions in flow
topic bromination
flow chemistry
Ramirez gem-dibromoolefination reaction
solid-supported reagent
triphenylphosphine monolith
url https://doi.org/10.3762/bjoc.9.207
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