Radical C−H Trifluoromethoxylation of (Hetero)arenes with Bis(trifluoromethyl)peroxide
| Autor: | Jonas R. Schmid, Matthew N. Hopkinson, Paul Golz, Sebastian Riedel, Stefan Dix |
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| Rok vydání: | 2021 |
| Předmět: |
Light
Hot Paper chemistry.chemical_element 010402 general chemistry 01 natural sciences Peroxide Catalysis chemistry.chemical_compound fluorine Atom economy Pyridine (hetero)arenes Trifluoromethyl 010405 organic chemistry Communication Organic Chemistry General Chemistry Combinatorial chemistry Communications Peroxides 0104 chemical sciences chemistry Reagent Photocatalysis Fluorine Indicators and Reagents trifluoromethoxylation TEMPO 500 Naturwissenschaften und Mathematik::540 Chemie::540 Chemie und zugeordnete Wissenschaften photocatalysis |
| Zdroj: | Chemistry (Weinheim an Der Bergstrasse, Germany) |
| ISSN: | 1521-3765 0947-6539 |
| DOI: | 10.1002/chem.202101621 |
| Popis: | Trifluoromethoxylated (hetero)arenes are of great interest for several disciplines, especially in agro‐ and medicinal chemistry. Radical C−H trifluoromethoxylation of (hetero)arenes represents an attractive approach to prepare such compounds, but the high cost and low atom economy of existing .OCF3 radical sources make them unsuitable for the large‐scale synthesis of trifluoromethoxylated building blocks. Herein, we introduce bis(trifluoromethyl)peroxide (BTMP, CF3OOCF3) as a practical and efficient trifluoromethoxylating reagent that is easily accessible from inexpensive bulk chemicals. Using either visible light photoredox or TEMPO catalysis, trifluoromethoxylated arenes could be prepared in good yields under mild conditions directly from unactivated aromatics. Moreover, TEMPO catalysis allowed for the one‐step synthesis of valuable pyridine derivatives, which have been previously prepared via multi‐step approaches. Bis(trifluoromethyl)peroxide (BTMP) is introduced as a new reagent for the C−H trifluoromethoxylation of arenes and heteroarenes. Readily accessed from inexpensive bulk chemicals, BTMP serves as a practical source of •OCF3 radicals upon activation through either visible light photoredox or TEMPO catalysis. Both methods deliver valuable fluorine‐containing building blocks in a single step from (hetero)aromatic feedstocks. |
| Databáze: | OpenAIRE |
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