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

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 temperatu...

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Bibliographic Details
Published in:Journal of organic chemistry 2020-05, Vol.85 (10), p.6380-6391
Main Authors: Simons, R. Thomas, Scott, Georgia E, Kanegusuku, Anastasia Gant, Roizen, Jennifer L
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c00139