Journal
ORGANIC LETTERS
Volume 22, Issue 21, Pages 8598-8602Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c03187
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Funding
- CAPES [001]
- CNPq [310514/2018-5]
- FAPEMIG
- FAPESP [2018/00106-7, 2013/07276-1]
- Rede Mineira de Quimica
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A novel electron-donor-acceptor (EDA) complex-enabled flow photochemical hydrotrifluoromethylation of unsaturated beta-keto esters is described. The developed protocol has an easy experimental procedure and does not require the use of transition-metal-based photocatalysts, allowing the isolation of 14 new compounds in up to 86% yield. Control experiments and computational studies revealed that the reaction proceeds through a Michael-type 1,4-addition of a trifluoromethyl radical, followed by a proton transfer step. Furthermore, the reaction could be scaled up to 1 mmol, and the final produce could be employed in the preparation of an isoxazolone and a pyrazolone as trifluoro-substituted heterocycles.
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