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Access to a new class of synthetic building blocks via trifluoromethoxylation of pyridines and pyrimidines
Since the first synthesis of trifluoromethyl ethers in 1935, the trifluoromethoxy (OCF ) group has made a remarkable impact in medicinal, agrochemical, and materials science research. However, our inability to facilely incorporate the OCF group into molecules, especially heteroaromatics, has limited...
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| Published in: | Chemical science (Cambridge) 2016-01, Vol.7 (1), p.424-429 |
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| Main Authors: | , , , , |
| Format: | Article |
| Language: | English |
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| cites | cdi_FETCH-LOGICAL-c477t-fd7bad14c9ae01d6dfcf0d54dc51c4c41d3b01e5dca027e07bb6fe9a3e5991443 |
| container_end_page | 429 |
| container_issue | 1 |
| container_start_page | 424 |
| container_title | Chemical science (Cambridge) |
| container_volume | 7 |
| creator | Feng, Pengju Lee, Katarzyna N Lee, Johnny W Zhan, Chengbo Ngai, Ming-Yu |
| description | Since the first synthesis of trifluoromethyl ethers in 1935, the trifluoromethoxy (OCF
) group has made a remarkable impact in medicinal, agrochemical, and materials science research. However, our inability to facilely incorporate the OCF
group into molecules, especially heteroaromatics, has limited its potential across a broad spectrum of technological applications. Herein, we report a scalable and operationally simple protocol for regioselective trifluoromethoxylation of a wide range of functionalized pyridines and pyrimidines under mild reaction conditions. The trifluoromethoxylated products are useful scaffolds that can be further elaborated by amidation and palladium-catalysed cross coupling reactions. Mechanistic studies suggest that a radical
-trifluoromethylation followed by the OCF
-migration reaction pathway is operable. Given the unique properties of the OCF
group and the ubiquity of pyridine and pyrimidine in biologically active molecules and functional materials, trifluoromethoxylated pyridines and pyrimidines could serve as valuable building blocks for the discovery and development of new drugs, agrochemicals, and materials. |
| doi_str_mv | 10.1039/c5sc02983j |
| format | article |
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-trifluoromethylation followed by the OCF
-migration reaction pathway is operable. Given the unique properties of the OCF
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-trifluoromethylation followed by the OCF
-migration reaction pathway is operable. Given the unique properties of the OCF
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group into molecules, especially heteroaromatics, has limited its potential across a broad spectrum of technological applications. Herein, we report a scalable and operationally simple protocol for regioselective trifluoromethoxylation of a wide range of functionalized pyridines and pyrimidines under mild reaction conditions. The trifluoromethoxylated products are useful scaffolds that can be further elaborated by amidation and palladium-catalysed cross coupling reactions. Mechanistic studies suggest that a radical
-trifluoromethylation followed by the OCF
-migration reaction pathway is operable. Given the unique properties of the OCF
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| fulltext | fulltext |
| identifier | ISSN: 2041-6520 |
| ispartof | Chemical science (Cambridge), 2016-01, Vol.7 (1), p.424-429 |
| issn | 2041-6520 2041-6539 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_5110255 |
| source | Open Access: PubMed Central |
| subjects | Agricultural chemicals Chemistry Cross coupling Ethers Pathways Pyridines Pyrimidines Radicals Synthesis |
| title | Access to a new class of synthetic building blocks via trifluoromethoxylation of pyridines and pyrimidines |
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