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Hydrocarbamoylation of Unsaturated Bonds by Nickel/Lewis-Acid Catalysis

Yoshiaki Nakao*, Hiroaki Idei, Kyalo Stephen Kanyiva and Tamejiro Hiyama*

*Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan, Email: yoshiakinakaonpc05.mbox.media.kyoto-u.ac.jp, thiyamakc.chuo-u.ac.jp

Y. Nakao, H. Idei, K. S. Kanyiva, T. Hiyama, J. Am. Chem. Soc., 2009, 131, 5070-5071.

DOI: 10.1021/ja901153s (free Supporting Information)


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Abstract

Formamides undergo addition reactions across alkynes and 1,3-dienes by nickel/Lewis acid catalysis to give stereo- and regioselectively various α,β- and β,γ-unsaturated amides. The presence of Lewis acid cocatalysts is crucial, and formamide coordination to the Lewis acid is considered to be responsible for the activation of their formyl C-H bonds probably through oxidative addition to nickel(0).

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Key Words

α,β-unsaturated compounds


ID: J48-Y2009-1290