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Hydrohalogenation of Unactivated Alkenes Using a Methanesulfonic Acid/Halide Salt Combination

Xavier Bertrand, Pascal Paquin, Laurent Chabaud, Jean-François Paquin*

*CCVC, PROTEO, Département de chimie, Université Laval, 1045 Avenue de la Médecine, Québec, Québec, G1V 0A6, Canada, Email:

X. Bertrand, P. Paquin, L. Chabaud, J.-F. Paquin, Synthesis, 2022, 54, 1413-1421.

DOI: 10.1055/s-0040-1719856

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The combination of methanesulfonic acid and inorganic halide salts (CaCl2, LiBr, LiI) mediates hydrochlorinations, hydrobrominations, and hydroiodinations of unactivated alkenes in acetic acid. This approach uses readily available and inexpensive reagents to provide alkyl halides in very good yields. An example of deuteriochlorination using deuterated acetic acid  as solvent is also demonstrated.

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Direct Hydrofluorination of Methallyl Alkenes Using a Methanesulfonic Acid/Triethylamine Trihydrofluoride Combination

X. Bertrand, J.-F. Paquin, Org. Lett., 2019, 21, 9759-9762.

Key Words

alkyl chlorides, alkyl bromides, alkyl iodides

ID: J66-Y2022