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.
A general method for the N-arylation of n class="Chemical">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.
Authors: Martins S Oderinde; Natalie H Jones; Antoine Juneau; Mathieu Frenette; Brian Aquila; Sharon Tentarelli; Daniel W Robbins; Jeffrey W Johannes Journal: Angew Chem Int Ed Engl Date: 2016-10-10 Impact factor: 15.336
Authors: Martin H Bolli; Christoph Boss; Christoph Binkert; Stephan Buchmann; Daniel Bur; Patrick Hess; Marc Iglarz; Solange Meyer; Josiane Rein; Markus Rey; Alexander Treiber; Martine Clozel; Walter Fischli; Thomas Weller Journal: J Med Chem Date: 2012-08-16 Impact factor: 7.446