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Morpholine Derivative Usable for Introduction of a Trifluoromethyl Group
4-[2,2,2-Trifluoro-1-[(trimethylsilyl)oxy]ethyl]morpholine (1) is a morpholine-derived hemiaminal ether and a useful trifluroromethlyating agent, first reported by Langlois et al. and Amii et al. independently. 1 acts as a nucleophilic CF3 source and anion equivalent. In the presence of catalytic CsF, the CF3 group of 1 nucleophilically can add to a variety of aromatic ketones and aldehydes with subsequent silylation of the carbonyl oxygen. Additionally, 1 can react with aryl iodides to add CF3 in the presence of if excess CsF and a Cu-catalyst to afford CF3-aryl species in high yield.
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References
- 1)New Stable Reagents for the Nucleophilic Trifluoromethylation. 1. Trifluoromethylation of Carbonyl Compounds with N-Formylmorpholine Derivatives
- 2)Copper-Catalyzed Aromatic Trifluoromethylation via Group Transfer from Fluoral Derivatives
