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Lactam Synthesis via the Intramolecular Hydroamidation of Alkynes Catalyzed by Palladium Complexes

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Nitin T. Patil, Zhibao Huo, Gan B. Bajracharya, and Yoshinori Yamamoto*

Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan yoshi@mail.tains.tohoku.ac.jp

J. Org. Chem., 2006, 71 (9), pp 3612–3614

DOI: 10.1021/jo060142x

Publication Date (Web): March 29, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

The palladium complexes catalyzed intramolecular hydroamidation reaction of amidoalkynes gives the corresponding lactams in good to high yields. For example, in the presence of 10 mol % of Pd(PPh₃)₄ and 20 mol % of PhCOOH, the reaction of the amidoalkyne 3a in 1,4-dioxane at 100 °C proceeded smoothly to give the corresponding lactam 4a in 92% yield.

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Published In Issue April 28, 2006
Received January 22, 2006

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Lactam Synthesis via the Intramolecular Hydroamidation of Alkynes Catalyzed by Palladium Complexes