Work

Photochemically-Mediated, Nickel-Catalyzed Synthesis of N-(Hetero)aryl Sulfamate Esters

Year: 2019

Type: article

Abstract: A general method is described for the coupling of (hetero)aryl bromides with O -alkyl sulfamate esters. The protocol relies on catalytic amounts of nickel and photoexcitable iridium complexes and proceeds under visible light irradiation at ambient temperature. This technology engages a broad range of simple and complex O -alkyl sulfamate ester substrates under mild conditions. Furthermore, it is possible to avoid undesirable N -alkylation, which was found to plague palladium-based protocols for N -arylation of O -alkyl sulfamate esters. These investigations represent the first use of sulfamate esters as nucleophiles in transition metal-catalyzed C–N coupling processes.

Source: Organic Letters

DOI: 10.1021/acs.orglett.9b02621

Authors: J. Miles Blackburn, Anastasia L. Gant Kanegusuku, Georgia E. Scott, Jennifer L. Roizen

Institution: Duke University

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green