Open AccessPhotochemically Mediated Nickel-Catalyzed Synthesis of N-(Hetero)aryl Sulfamides
Author(s) -
R. Thomas Simons,
Georgia Scott,
Anastasia Gant Kanegusuku,
Jennifer L. Roizen
Publication year - 2020
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.0c00139
Subject(s) - aryl , chemistry , catalysis , combinatorial chemistry , nickel , coupling reaction , organic chemistry , alkyl
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)]PF 6 as a photosensitizer, NiBr 2 ·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.