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Continuous Flow Chlorination of Alkenyl Iodides Promoted by Copper Tubing

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

*Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec, H3C 3J7, Canada; Université libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium, Email: andre.charetteumontreal.ca, helene.lebelumontreal.ca, Gwilherm.Evanoulb.be

A. Nitelet, V. Kairouz, H. Lebel, A. B. Charette, G. Evano, Synthesis, 2019, 51, 251-257.

DOI: 10.1055/s-0037-1610398 (free Supporting Information)


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Abstract

The use of copper tubings enables a simple continuous flow synthesis of alkenyl chlorides in very good yields from the corresponding readily available alkenyl iodides with full retention of the double bond geometry. The reaction time was reduced 24 to 48fold compared to the batch process.

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A General Copper-Catalyzed Vinylic Halogen Exchange Reaction

A. Nitelet, G. Evano, Org. Lett., 2016, 18, 1904-1907.


Key Words

copper catalysis, heterogeneous catalysis, vinyl chlorides, halogen exchange, Finkelstein reaction, flow chemistry


ID: J66-Y2019