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

Kurose, Ryo; Nishii, Yuji; Miura, Masahiro

Organic Letters, 2021, 23(6), 2380-2385

Number of Access:284（2025-08-14 02:10 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/92810

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Title
Metal-Free Direct Trifluoromethylthiolation of Aromatic Compounds Using Triptycenyl Sulfide Catalyst
Creator
CreatorName
Kurose, Ryo
NRID
1000070773787 1000070773787
ORCID
0000-0002-6824-0639 0000-0002-6824-0639
researchmap permalink
y_nishii y_nishii
Scopus Author ID
55233363700 55233363700
CreatorName
Nishii, Yuji
NRID
1000020183626 1000020183626
ORCID
0000-0001-8288-6439 0000-0001-8288-6439
researchmap permalink
read0013936 read0013936
Scopus Author ID
7402799909 7402799909
CreatorName
Miura, Masahiro
Description
Kurose R., Nishii Y., Miura M.. Metal-Free Direct Trifluoromethylthiolation of Aromatic Compounds Using Triptycenyl Sulfide Catalyst. Organic Letters. 23(6), 2380-2385, (2021), 19 March 2021; ©2021 American Chemical Society. https://doi.org/10.1021/acs.orglett.1c00727.
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 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 substitu-tion effect on the catalytic activity.
Publisher
American Chemical Society
Source Title
Organic Letters
Volume (Issue)
23(6)
Page
2380-2385
Date of Issued
2021-03-19
Language
English
Handle URL
https://hdl.handle.net/11094/92810
PISSN
15237060
eISSN
15237052
NCID
AA11347843
Relation.isVersionOf
DOI (Publisher Version)
https://doi.org/10.1021/acs.orglett.1c00727
Access Rights
open access
CopyRight
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.1c00727.
oaire:version
Accepted Manuscript
Category
学術雑誌論文 Journal Article