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
a  Laboratoire 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
b  Centre 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
,
b  Centre 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
,
b  Centre 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
,
a  Laboratoire 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
› Author Affiliations
This research was supported by the Fonds pour la formation à la Recherche dans l’Industrie et dans l’Agriculture (F.R.I.A., graduate fellowship to A.N.), the Natural Science and Engineering Research Council of Canada (NSERC) under the CREATE Training Program in Continuous Flow Science (CREATE 449307-2014), and the ‘G-3 des universités francophones’ (Chimie en flux continu et catalyse - C3F).
Further Information

Publication History

Received: 25 October 2018

Accepted: 05 November 2018

Publication Date:
30 November 2018 (online)

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.

Supporting Information

 
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