Copper-catalyzed intramolecular iminolactonization cyclization reactions of remote C(sp3)–H bonds in carboxamides. Issue 45 (2nd November 2022)

• Record Type: Journal Article
• Authors: Wei, He; Zhang, Zhenhua; Zhang, Xiang; Gao, Shuo; Wang, Tongtong; Zhao, Mengmeng; Wei, Pifeng; Wang, Min
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 45(2022)
• Page Start: 8912
• Page End: 8916
• Publication Date: 2022-11-02
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob01711c
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A novel and efficient synthetic method for iminolactones by copper-catalyzed intramolecular C(sp 3 )–H bond functionalization of carboxamides via a cascade process is reported for the first time. Abstract : Iminolactones are an important class of heterocyclic compounds. Thus, the development of an efficient strategy for their preparation becomes highly desirable. A new method for the transformation of carboxamides into iminolactones via copper-catalyzed intramolecular C(sp 3 )–H bond functionalization is reported herein. A series of primary, secondary and tertiary C(sp 3 )–H bonds were all accommodated to afford iminolactones through a cascade process which involves amidyl radical intermediate generation, 1, 5-HAT (hydrogen atom transfer), and ensuing cyclization.