Trifluoromethyl Thianthrenium Triflate: A Readily Available Trifluoromethylating Reagent with Formal CF(3)(+), CF(3)(•), and CF(3)(–) Reactivity

[Image: see text] Here we report the synthesis and application of trifluoromethyl thianthrenium triflate (TT-CF(3)(+)OTf(–)) as a novel trifluoromethylating reagent, which is conveniently accessible in a single step from thianthrene and triflic anhydride. We demonstrate the use of TT-CF(3)(+)OTf(–)...

Descripción completa

Detalles Bibliográficos
Autores principales: Jia, Hao, Häring, Andreas P., Berger, Florian, Zhang, Li, Ritter, Tobias
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8297735/
https://www.ncbi.nlm.nih.gov/pubmed/33985330
http://dx.doi.org/10.1021/jacs.1c02606
_version_ 1783725913576308736
author Jia, Hao
Häring, Andreas P.
Berger, Florian
Zhang, Li
Ritter, Tobias
author_facet Jia, Hao
Häring, Andreas P.
Berger, Florian
Zhang, Li
Ritter, Tobias
author_sort Jia, Hao
collection PubMed
description [Image: see text] Here we report the synthesis and application of trifluoromethyl thianthrenium triflate (TT-CF(3)(+)OTf(–)) as a novel trifluoromethylating reagent, which is conveniently accessible in a single step from thianthrene and triflic anhydride. We demonstrate the use of TT-CF(3)(+)OTf(–) in electrophilic, radical, and nucleophilic trifluoromethylation reactions.
format Online
Article
Text
id pubmed-8297735
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-82977352021-07-23 Trifluoromethyl Thianthrenium Triflate: A Readily Available Trifluoromethylating Reagent with Formal CF(3)(+), CF(3)(•), and CF(3)(–) Reactivity Jia, Hao Häring, Andreas P. Berger, Florian Zhang, Li Ritter, Tobias J Am Chem Soc [Image: see text] Here we report the synthesis and application of trifluoromethyl thianthrenium triflate (TT-CF(3)(+)OTf(–)) as a novel trifluoromethylating reagent, which is conveniently accessible in a single step from thianthrene and triflic anhydride. We demonstrate the use of TT-CF(3)(+)OTf(–) in electrophilic, radical, and nucleophilic trifluoromethylation reactions. American Chemical Society 2021-05-14 2021-05-26 /pmc/articles/PMC8297735/ /pubmed/33985330 http://dx.doi.org/10.1021/jacs.1c02606 Text en © 2021 The Authors. Published by American Chemical Society Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Jia, Hao
Häring, Andreas P.
Berger, Florian
Zhang, Li
Ritter, Tobias
Trifluoromethyl Thianthrenium Triflate: A Readily Available Trifluoromethylating Reagent with Formal CF(3)(+), CF(3)(•), and CF(3)(–) Reactivity
title Trifluoromethyl Thianthrenium Triflate: A Readily Available Trifluoromethylating Reagent with Formal CF(3)(+), CF(3)(•), and CF(3)(–) Reactivity
title_full Trifluoromethyl Thianthrenium Triflate: A Readily Available Trifluoromethylating Reagent with Formal CF(3)(+), CF(3)(•), and CF(3)(–) Reactivity
title_fullStr Trifluoromethyl Thianthrenium Triflate: A Readily Available Trifluoromethylating Reagent with Formal CF(3)(+), CF(3)(•), and CF(3)(–) Reactivity
title_full_unstemmed Trifluoromethyl Thianthrenium Triflate: A Readily Available Trifluoromethylating Reagent with Formal CF(3)(+), CF(3)(•), and CF(3)(–) Reactivity
title_short Trifluoromethyl Thianthrenium Triflate: A Readily Available Trifluoromethylating Reagent with Formal CF(3)(+), CF(3)(•), and CF(3)(–) Reactivity
title_sort trifluoromethyl thianthrenium triflate: a readily available trifluoromethylating reagent with formal cf(3)(+), cf(3)(•), and cf(3)(–) reactivity
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8297735/
https://www.ncbi.nlm.nih.gov/pubmed/33985330
http://dx.doi.org/10.1021/jacs.1c02606
work_keys_str_mv AT jiahao trifluoromethylthianthreniumtriflateareadilyavailabletrifluoromethylatingreagentwithformalcf3cf3andcf3reactivity
AT haringandreasp trifluoromethylthianthreniumtriflateareadilyavailabletrifluoromethylatingreagentwithformalcf3cf3andcf3reactivity
AT bergerflorian trifluoromethylthianthreniumtriflateareadilyavailabletrifluoromethylatingreagentwithformalcf3cf3andcf3reactivity
AT zhangli trifluoromethylthianthreniumtriflateareadilyavailabletrifluoromethylatingreagentwithformalcf3cf3andcf3reactivity
AT rittertobias trifluoromethylthianthreniumtriflateareadilyavailabletrifluoromethylatingreagentwithformalcf3cf3andcf3reactivity

Ejemplares similares