4.7 Article

Ni-Catalyzed C(sp2)-H alkylation of N-quinolylbenzamides using alkylsilyl peroxides as structurally diverse alkyl sources

Journal

CHEMICAL COMMUNICATIONS
Volume 57, Issue 64, Pages 7942-7945

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d1cc02983e

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Funding

  1. JSPS KAKENHI [JP17H06450, JP20H04815]

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This study describes a Ni-catalyzed direct C-H alkylation of N-quinolylbenzamides using alkylsilyl peroxides as alkyl-radical precursors. The reaction forms a new C(sp(3))-C(sp(2)) bond via selective cleavage of both C(sp(3))-C(sp(3)) and C(sp(2))-H bonds. 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.
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.

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