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

James A. Bull and André B. Charette*

*Département de Chimie, Université de Montréal, PO Box 6128, Station Downtown, Montréal, Québec, Canada H3C 3J7, Email: andre.charetteumontreal.ca

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

DOI: 10.1021/jo8014616

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Abstract

Alkylation of NaCHI₂ with alkyl iodides and LiCHI₂ with allyl and benzyl bromides gives functionalized gem-diiodoalkanes in good to excellent yields. Functional group tolerance toward olefins, acetals, ethers and silyl ethers, carbamates, and hindered esters is demonstrated.

see article for more examples

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

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

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Key Words

Diiodomethylation

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ID: J42-Y2008-3070