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


Journal Article

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.

Full Text

Duke Authors

Cited Authors

  • Blackburn, JM; Gant Kanegusuku, AL; Scott, GE; Roizen, JL

Published Date

  • August 22, 2019

Published In

PubMed ID

  • 31436104

Pubmed Central ID

  • 31436104

Electronic International Standard Serial Number (EISSN)

  • 1523-7052

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/acs.orglett.9b02621


  • eng