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Intramolecular 1,5-C(sp³)-H Radical Amination via Co(II)-Based Metalloradical Catalysis for Five-Membered Cyclic Sulfamides.

ABSTRACT: Co(II)-based metalloradical catalysis (MRC) proves effective for intramolecular 1,5-C-H amination of sulfamoyl azides under neutral and nonoxidative conditions, providing a straightforward approach to access strained 5-membered cyclic sulfamides with nitrogen gas as the only byproduct. The metalloradical amination system is applicable to different types of C(sp³)-H bonds and has a high degree of functional group tolerance. Additional features of the Co(II)-catalyzed 1,5-C-H amination include excellent chemoselectivity toward allylic and propargylic C-H bonds. The unique reactivity and selectivity profile of the Co(II)-catalyzed 1,5-C-H amination is attributed to the underlying radical mechanism of MRC.

SUBMITTER: Lu H

PROVIDER: S-EPMC5271564 | biostudies-literature | 2016

REPOSITORIES: biostudies-literature

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Intramolecular 1,5-C(sp3)-H Radical Amination via Co(II)-Based Metalloradical Catalysis for Five-Membered Cyclic Sulfamides.

Lu Hongjian H Lang Kai K Jiang Huiling H Wojtas Lukasz L Zhang X Peter XP

Chemical science 20160728 12

Co(II)-based metalloradical catalysis (MRC) proves effective for intramolecular 1,5-C-H amination of sulfamoyl azides under neutral and nonoxidative conditions, providing a straightforward approach to access strained 5-membered cyclic sulfamides with nitrogen gas as the only byproduct. The metalloradical amination system is applicable to different types of C(sp3)-H bonds and has a high degree of functional group tolerance. Additional features of the Co(II)-catalyzed 1,5-C-H amination ...[more]

PMID: 28138382

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