Photochemically Mediated Nickel-Catalyzed Synthesis of N-(Hetero)aryl Sulfamides.


Journal Article

A general method for the N-arylation of sulfamides with aryl bromides is described. The protocol leverages a dual-catalytic system, with [Ir(ppy)2(dtbbpy)]PF6 as a photosensitizer, NiBr2·glyme as a precatalyst, and 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU) as a base, and proceeds at room temperature under visible light irradiation. Using these tactics, aryl boronic esters and aryl chlorides can be carried through the reaction untouched. The developed reactions efficiently engage simple bromoarenes and primary sulfamides in between 66% and quantitative yields. For more challenging substrates, such as secondary sulfamides, the reaction efficiency is documented. Thereby, these methods complement the known Buchwald-Hartwig coupling methods for N-arylation of sulfamides.

Full Text

Duke Authors

Cited Authors

  • Simons, RT; Scott, GE; Kanegusuku, AG; Roizen, JL

Published Date

  • May 2020

Published In

Volume / Issue

  • 85 / 10

Start / End Page

  • 6380 - 6391

PubMed ID

  • 32312047

Pubmed Central ID

  • 32312047

Electronic International Standard Serial Number (EISSN)

  • 1520-6904

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/acs.joc.0c00139


  • eng