Convenient One-Pot Synthesis of (E)-β-Aryl Vinyl Halides from Benzyl Bromides and Dihalomethanes

James A. Bull, James J. Mousseau and André B. Charette*

*Department of Chemistry, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Quebec, Canada H3C 3J7, Email: andre.charetteumontreal.ca

J. A. Bull, J. J. Mousseau, A. B. Charette, Org. Lett., 2008, 10, 5485-5488.

DOI: 10.1021/ol802315k

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Abstract

(E)-β-Aryl vinyl halides are synthesized in good yield with excellent stereoselectivity and functional group tolerance from benzyl bromides. The convenient conditions involve a nucleophilic substitution with anions of CH₂I₂, ICH₂Cl, or CH₂Br₂ and a subsequent stereoselective base-induced elimination. A facile purification allows rapid access to a wide range of functionalized vinyl halides.

see article for more examples

proposed stereoselective elimination of HY from a gem-dihalide intermediate

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Improved Procedure for the Synthesis of gem-Diiodoalkanes by the Alkylation of Diiodomethane. Scope and Limitations

J. A. Bull, A. B. Charette, J. Org. Chem., 2008, 73, 8097-8100.

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Key Words

alkenyl halides

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ID: J54-Y2008-3760