TFA-Promoted Intermolecular Friedel-Crafts Alkylation of Arenes with 2,2,2-Trifluoroethylaryl Sulfoxides.

Authors :: Deng Z
Qiu LY
Pan W
Qian B
Chen J
Zhang H
Chen QY
Cao W
Tang XJ
Source :: Chemistry, an Asian journal [Chem Asian J] 2022 Jul 15; Vol. 17 (14), pp. e202200190. Date of Electronic Publication: 2022 Jun 10.
Publication Year :: 2022
Abstract: The classical Pummerer rearrangement of 2,2,2-trifluoroethylaryl sulfoxide with trifluoracetic anhydride (TFAA) affords the S,O-acetal efficiently. In the presence of trifluoracetic acid (TFA) as the co-solvent, the S,O-acetal can regenerate reactive thionium intermediate of Pummerer rearrangement. When employing arenes as nucleophiles, this strategy produces corresponding 1-thiyl-2,2,2-trifluoroethyl arenes with excellent yields under metal-free conditions.<br /> (© 2022 Wiley-VCH GmbH.)

Full Text Access

Tools