Copper-Catalyzed Intramolecular Olefinic C(sp<sup>2</sup>)–H Amidation for the Synthesis of <i>γ</i>-Alkylidene-<i>γ</i>-lactams
Kanako Nozawa-Kumada,
Masahito Hayashi,
Eunsang Kwon,
Masanori Shigeno,
Akira Yada,
Yoshinori Kondo
Affiliations
Kanako Nozawa-Kumada
Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aoba, Aramaki, Aoba-ku, Sendai 980-8578, Miyagi, Japan
Masahito Hayashi
Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aoba, Aramaki, Aoba-ku, Sendai 980-8578, Miyagi, Japan
Eunsang Kwon
Endowed Research Laboratory of Dimensional Integrated Nanomaterials, Graduate School of Science, Tohoku University, Aoba-ku, Sendai 980-8578, Miyagi, Japan
Masanori Shigeno
Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aoba, Aramaki, Aoba-ku, Sendai 980-8578, Miyagi, Japan
Akira Yada
Interdisciplinary Research Center for Catalytic Chemistry, National Institute of Advanced Industrial Science and Technology (AIST), Central 5, 1-1-1 Higashi, Tsukuba 305-8565, Ibaraki, Japan
Yoshinori Kondo
Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aoba, Aramaki, Aoba-ku, Sendai 980-8578, Miyagi, Japan
Herein, we report the copper-catalyzed dehydrogenative C(sp2)–N bond formation of 4-pentenamides via nitrogen-centered radicals. This reaction provides a straightforward and efficient preparation method for γ-alkylidene-γ-lactams. Notably, we could controllably synthesize α,β-unsaturated- or α,β-saturated-γ-alkylidene-γ-lactams depending on the reaction conditions.
