Copper-Catalyzed Intramolecular Olefinic C(sp2)–H Amidation for the Synthesis of γ-Alkylidene-γ-lactams-Reference-Cited by-同舟云学术

Copper-Catalyzed Intramolecular Olefinic C(sp2)–H Amidation for the Synthesis of γ-Alkylidene-γ-lactams

Published:2023-09-18 Issue:18 Volume:28 Page:6682
ISSN:1420-3049
Container-title:Molecules
language:en
Short-container-title:Molecules

Author:

Nozawa-Kumada Kanako¹²^ORCID,Hayashi Masahito¹,Kwon Eunsang³⁴^ORCID,Shigeno Masanori¹⁵^ORCID,Yada Akira²^ORCID,Kondo Yoshinori¹^ORCID

Affiliation:

1. Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aoba, Aramaki, Aoba-ku, Sendai 980-8578, Miyagi, Japan

2. 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

3. Endowed Research Laboratory of Dimensional Integrated Nanomaterials, Graduate School of Science, Tohoku University, Aoba-ku, Sendai 980-8578, Miyagi, Japan

4. Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Aoba-ku, Sendai 980-8578, Miyagi, Japan

5. Japan Science and Technology Agency (JST), Precursory Research for Embryonic Science and Technology (PRESTO), Kawaguchi 332-0012, Saitama, Japan

Abstract

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.

Funder

JSPS KAKENHI Grant-in-Aid for Scientific Research

Transformative Research Areas (A) Digi-TOS

Takeda Science Foundation

Iwatani Naoji Foundation

Astellas Foundation for Research on Metabolic Disorders

SEI Group CSR Foundation

Uehara Memorial Foundation

creation of science technology innovation

Publisher

MDPI AG

Subject

Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science

Link

https://www.mdpi.com/1420-3049/28/18/6682/pdf

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