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 (free Supporting Information)
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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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