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A General Copper-Catalyzed Vinylic Halogen Exchange Reaction

Antoine Nitelet and Gwilherm Evano*

*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:

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

DOI: 10.1021/acs.orglett.6b00678

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The use of catalytic amounts of copper iodide and trans-N,N′-dimethylcyclohexane-1,2-diamine in the presence of tetramethylammonium chloride or bromide enables the transformation of easily accessible alkenyl iodides into their far less available chlorinated and brominated derivatives in excellent yields and with full retention of the double bond geometry.

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Continuous Flow Chlorination of Alkenyl Iodides Promoted by Copper Tubing

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

Key Words

vinyl chlorides, vinyl bromides

ID: J54-Y2016