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Metal-Free Direct Trifluoromethylthiolation of Aromatic Compounds Using Triptycenyl Sulfide Catalyst

Authors :
Kurose, Ryo
Nishii, Yuji
Miura, Masahiro
Source :
Organic Letters; March 2021, Vol. 23 Issue: 6 p2380-2385, 6p
Publication Year :
2021

Abstract

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 SCF3fragment through the formation of sulfonium intermediates. This method enables direct installation of an SCF3group 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.

Details

Language :
English
ISSN :
15237060 and 15237052
Volume :
23
Issue :
6
Database :
Supplemental Index
Journal :
Organic Letters
Publication Type :
Periodical
Accession number :
ejs55591363
Full Text :
https://doi.org/10.1021/acs.orglett.1c00727