One-Pot Synthesis of 1-Iodoalkynes and Trisubstituted Alkenes from Benzylic and Allylic Bromides

Guillaume Pelletier, Sharon Lie, James J. Mousseau and André B. Charette*

*Centre in Green Chemistry and Catalysis, Department of Chemistry, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec, Canada H3C 3J7, Email: andre.charetteumontreal.ca

G. Pelletier, S. Lie, J. J. Mousseau, A. B. Charette, Org. Lett., 2012, 14, 5464-5467.

DOI: 10.1021/ol302544s

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Abstract

Reaction of readily accessible benzylic and allylic alkyl bromides with iodoform followed by a one-pot double elimination procedure enables a triphenylphosphine-free synthesis of 1-iodoalkynes including facile purification compared with Corey-Fuchs iodoalkynylation conditions. Replacing CHI₃ with CHI₂Cl allows the isolation of gem-(Z)-chloro-(E)-iodoalkenes. The use of benzhydryl bromides as nucleophiles leads to trisubstituted alkenes.

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Key Words

Iodoalkynes, Enynes

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ID: J54-Y2012-3480