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: jean-francois.paquin
chm.ulaval.ca
X. Bertrand, P. Paquin, L. Chabaud, J.-F. Paquin, Synthesis, 2022, 54, 1413-1421.
DOI: 10.1055/s-0040-1719856
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Abstract
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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X. Bertrand, J.-F. Paquin, Org. Lett., 2019, 21, 9759-9762.
Synthesis of Tertiary Fluorides through an Acid-Mediated Deoxyfluorination of Tertiary Alcohols
X. Bertrand, M. Pucheault, L. Chabaud, J.-F. Paquin, J. Org. Chem., 2023, 88, 14527-14539.
Key Words
alkyl chlorides, alkyl bromides, alkyl iodides
ID: J66-Y2022
