Ni-Catalyzed C(sp2)–H alkylation of N-quinolylbenzamides using alkylsilyl peroxides as structurally diverse alkyl sources. Issue 64 (20th July 2021)

• Record Type: Journal Article
• Authors: Tsuzuki, Saori; Sakurai, Shunya; Matsumoto, Akira; Kano, Taichi; Maruoka, Keiji
• Is Part Of: Chemical communications. Volume 57:Issue 64(2021)
• Page Start: 7942
• Page End: 7945
• Publication Date: 2021-07-20
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d1cc02983e
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : A Ni-catalyzed direct C–H alkylation of N -quinolylbenzamides using alkylsilyl peroxides as alkyl-radical precursors is described. Abstract : A Ni-catalyzed direct C–H alkylation of N -quinolylbenzamides using alkylsilyl peroxides as alkyl-radical precursors is described. The reaction forms a new C(sp 3 )–C(sp 2 ) bond via the selective cleavage of both C(sp 3 )–C(sp 3 ) and C(sp 2 )–H bonds. This transformation shows a high functional-group tolerance and, due to the structural diversity of alkylsilyl peroxides, a wide range of alkyl chains including functional groups and complex structures can be introduced at the ortho -position of readily available N -quinolylbenzamide derivatives. Mechanistic studies suggest that the reaction involves a radical mechanism.