Iridium-Catalyzed Addition of Aroyl Chlorides and Aliphatic Acid Chlorides to Terminal Alkynes

Tomohiro Iwai, Tetsuaki Fujihara, Jun Terao and Yasushi Tsuji*

*Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan, Email: ytsujiscl.kyoto-u.ac.jp

T. Miura, T. Biyajima, T. Fujii, M. Murakami, J. Am. Chem. Soc., 2012, 134, 194-196.

DOI: 10.1021/ja209679c

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Abstract

Iridium complexes show high catalytic activity in regio- and stereoselective intermolecular additions of acid chlorides to terminal alkynes to afford valuable (Z)-β-chloro-α,β-unsaturated ketones. Whereas a N-heterocyclic carbene (NHC) is an efficient ligand for the addition of aroyl chlorides, dicyclohexyl(2-methylphenyl)phosphine (PCy₂(o-Tol)) enables the reaction of aliphatic acid chlorides.

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Key Words

Enones, Vinyl Chlorides

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ID: J48-Y2012-0150