Silver Catalyzed Site-Selective C(sp³)−H Bond Amination of Secondary over Primary C(sp³)−H Bonds

Abstract

Sulfamates are widespread in numerous pharmacologically active molecules. In this paper, Silver/Bathophenanthroline catalyzed the intramolecular selective amination of primary C(sp3)−H bonds and secondary C(sp3)−H bonds of sulfamate esters, to produce cyclic sulfamates in good yields and with a high site-selectivity. DFT calculations revealed that the interaction between sulfamates and L10 makes the molecule more firmly attached to the catalyst, benefiting the catalysis reaction. The in vitro anticancer activity of the final products was evaluated in MCF-7 breast cancer cells.

Keywords

• silver-catalyzed nitrene
• intramolecular selective amination
• cyclic sulfamate derivatives
• primary C(sp³)−H bond