Continuous Flow Chlorination of Alkenyl Iodides Promoted by Copper Tubing

Antoine Nitelet; Vanessa Kairouz; Hélène Lebel; André B. Charette; Gwilherm Evano

doi:10.1055/s-0037-1610398

Synthesis, Table of Contents

CC BY-ND-NC 4.0 · Synthesis 2019; 51(01): 251-257
DOI: 10.1055/s-0037-1610398

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Continuous Flow Chlorination of Alkenyl Iodides Promoted by Copper Tubing

Antoine Nitelet

^aLaboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium Email: Gwilherm.Evano@ulb.be

,

Vanessa Kairouz

^bCentre in Green Chemistry and Catalysis, Faculty of Arts and Sciences, Department of Chemistry, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec, H3C 3J7, Canada Email: andre.charette@umontreal.ca Email: helene.lebel@umontreal.ca

,

Hélène Lebel *

^bCentre in Green Chemistry and Catalysis, Faculty of Arts and Sciences, Department of Chemistry, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec, H3C 3J7, Canada Email: andre.charette@umontreal.ca Email: helene.lebel@umontreal.ca

,

André B. Charette *

^bCentre in Green Chemistry and Catalysis, Faculty of Arts and Sciences, Department of Chemistry, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec, H3C 3J7, Canada Email: andre.charette@umontreal.ca Email: helene.lebel@umontreal.ca

,

Gwilherm Evano *

^aLaboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium Email: Gwilherm.Evano@ulb.be

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Abstract

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Abstract

A simple continuous flow synthesis of alkenyl chlorides from the corresponding readily available alkenyl iodides in copper reactor tubing is described. A variety of alkenyl chlorides were obtained in good to excellent yields with full retention of the double bond geometry. The reaction time was reduced by a factor of 24–48 compared to the batch process.

Key words

copper catalysis - heterogeneous catalysis - halogen exchange - Finkelstein reaction - continuous flow process

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