Work

Organocatalytic nitrenoid transfer: metal-free selective intermolecular C(sp 3 )–H amination catalyzed by an iminium salt

Year: 2017

Type: article

Abstract: )-H amination. The method utilizes a trifluoromethyl iminium salt as the catalyst, iminoiodinanes as the nitrogen source, and substrate as the limiting reagent. Activated, benzylic, and aliphatic substrates can all be selectively functionalized in yields up to 87%. A mechanistic proposal for the observed reactivity supported by experimental evidence invokes the intermediacy of a diaziridinium salt or related organic nitrenoid, species that have not been previously explored for the purpose of C-H amination. Finally, examples of late-stage functionalization of complex molecules highlight the selectivity and potential utility of this catalytic method in synthesis.

Source: Chemical Science

DOI: 10.1039/c7sc03968a

Authors: Logan A. Combee, Balaram Raya, Daoyong Wang, Michael K. Hilinski

Institution: University of Virginia

Language: English

Topic: Synthesis and Catalytic Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funders: University of Virginia, National Institutes of Health, National Institute of General Medical Sciences

Award: Organocatalytic Site-Selective C-H Bond Functionalization