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...
Main Authors: | , , |
---|---|
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 |
_version_ | 1818343891657555968 |
---|---|
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. |
first_indexed | 2024-12-13T16:37:47Z |
format | Article |
id | doaj.art-f8f1382dbafe45aa8dffdb56e8f0261d |
institution | Directory Open Access Journal |
issn | 1860-5397 |
language | English |
last_indexed | 2024-12-13T16:37:47Z |
publishDate | 2013-09-01 |
publisher | Beilstein-Institut |
record_format | Article |
series | Beilstein Journal of Organic Chemistry |
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 |
work_keys_str_mv | AT kimberleyaroper theapplicationofamonolithictriphenylphosphinereagentforconductingramirezgemdibromoolefinationreactionsinflow AT malcolmbberry theapplicationofamonolithictriphenylphosphinereagentforconductingramirezgemdibromoolefinationreactionsinflow AT stevenvley theapplicationofamonolithictriphenylphosphinereagentforconductingramirezgemdibromoolefinationreactionsinflow AT kimberleyaroper applicationofamonolithictriphenylphosphinereagentforconductingramirezgemdibromoolefinationreactionsinflow AT malcolmbberry applicationofamonolithictriphenylphosphinereagentforconductingramirezgemdibromoolefinationreactionsinflow AT stevenvley applicationofamonolithictriphenylphosphinereagentforconductingramirezgemdibromoolefinationreactionsinflow |