Metal-Free Direct Trifluoromethylthiolation of Aromatic Compounds Using Triptycenyl Sulfide Catalyst
Herein we report an efficient synthetic method for the electrophilic trifluoromethylthiolation of aromatic compounds. The key is to use triptycenyl sulfide (Trip-SMe) and TfOH to enhance the electrophilicity of SCF3 fragment through the formation of sulfonium intermediates. This method enables direct installation of an SCF3 group onto unactivated aromatics at room temperature, adopting a commercially available saccharin-based reagent. Preliminary DFT calculation was carried out to investigate the substitution effect on the catalytic activity.
Kurose, Ryo,Nishii, Yuji,Miura, Masahiro
supporting information
p. 2380 - 2385
(2021/04/05)
Silver-Mediated Trifluoromethylthiolation-Iodination of Arynes
(Chemical Equation Presented). A one-pot trifluoromethylthiolation-iodination of arynes with trifluoromethylthiosilver (AgSCF3) and 1-iodophenylacetylene is described. This protocol allows rapid construction of o-trifluoromethylthiolated arene building blocks in moderate yields. These products were found to be excellent precursors for Yagupolskii-Umemoto-type electrophilic trifluoromethylation reagents.
Zeng, Yuwen,Hu, Jinbo
supporting information
p. 856 - 859
(2016/03/04)
Pd-catalyzed synthesis of Ar-SCF3 compounds under mild conditions
Good to excellent yields of aryl trifluoromethyl sulfides, which are an important class of compounds in both the pharmaceutical and agrochemical areas, can be achieved under mild conditions by the Pd-catalyzed reaction of aryl bromides with a trifluoromethylthiolate nucleophile (see scheme). Copyright
Teverovskiy, Georgiy,Surry, David S.,Buchwald, Stephen L.
supporting information; experimental part
p. 7312 - 7314
(2011/10/03)
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