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Indium-Catalyzed 2-Alkenylation of 1,3-Dicarbonyl Compounds with Unactivated Alkynes

Kohei Endo, Takuji Hatakeyama, Masaharu Nakamura and Eiichi Nakamura*

*Department of Chemistry, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan, Email:

K. Endo, T. Hatakeyama, M. Nakamura, E. Nakamura, J. Am. Chem. Soc., 2007, 129, 5264-5271.

DOI: 10.1021/ja0702014

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1,3-Dicarbonyl compounds add to unactivated alkynes in the presence of less than 1 mol-% of indium(III) trifluoromethanesulfonate in high to excellent yield to give 2-alkenylated 1,3-dicarbonyl compounds. This mild reaction does not require solvent and tolerates various functional groups.

see article for more examples

Stereoselective Synthesis of Trisubstituted E-Iodoalkenes by Indium-Catalyzed syn-Addition of 1,3-Dicarbonyl Compounds to 1-Iodoalkynes

H. Tsuji, T. Fujimoto, K. Endo, M. Nakamura, E. Nakamura, Org. Lett., 2008, 10, 1219-1221.

Indium Triflate-Catalyzed Vinylation of β-Ketoesters with Acetylene Gas

M. Nakamura, K. Endo, E. Nakamura, Org. Lett., 2005, 7, 3279-3281.

Key Words

alkenylation, active methylenes

ID: J48-Y2007-1330