## 2 Experimental Section
### General Procedure for the Preparation of Selectively Fluorinated Ketones [10,13]
The organic layers were combined, washed with deionized water, and the organic layer dried over Na\({}_{2}\)SO\({}_{4}\). The solvent was evaporated under reduced pressure, providing a orange solid, which when subjected to radial chromatography, gave a fraction which upon recrystallization, yielded pale, orange crystals (CH\({}_{2}\)Cl\({}_{2}\)), **3d**, in 45% yield, m.p. 80-83 \({}^{\circ}\)C. An additional fraction was collected which contained unreacted **3b** and **3c**. **3d**: NMR: \({}^{1}\)H: \(\delta\), 7.25-8.05 (6H, m), 14.83 (1H, bs). \({}^{13}\)C: \(\delta\) 119.3 (CF\({}_{3}\), q, \({}^{1}\)J\({}_{\rm C-F}\) = 284 Hz), 124.9, 125.4, 126.9, 129.9, 130.1, 130.4, 131.4, 135.1, 139.1, 157.3, 184.6 (C-CF\({}_{3}\), q, \({}^{2}\)J\({}_{\rm C-F}\) = 35 Hz). \({}^{19}\)F (C\({}_{6}\)F\({}\) ext. std. ): \(\delta\)\(-\)74.25 (s, 3F). Analysis calcd for C\({}_{12}\)H\({}_{7}\)F\({}_{3}\)OC, 60.01, H, 2.94. Found: C, 60.13, H, 2.88. 4,4,4-trifluoro-1-(1-oxotetrahydronaphthlyl)-1,3-butanedione (**4b**) [17]. A 100 mL round bottom flask is charged with 50 mL dry Et\({}_{2}\)O, 5 mL dry diisopropylamine, equipped with a magnetic stir bar and placed under N\({}_{2}\) at 0 \({}^{\circ}\)C. To this is added LDA (6.0 mL, 0.0120 mol) and stirred for fifteen minutes. Then, a solution of **4a** (0.752 g, 0.004 mol) in 15 mL dry Et\({}_{2}\)O is added dropwise slowly via syringe. After 8 h, ethyl trifluoroacetate (0.96 mL, 0.008 mol) is delivered dropwise slowly via syringe, the reaction mixture is stirred overnight and allowed to warm to rt. A third equivalent of ethyl trifluoroacetate (0.004 mol) is added after 24 hours and the solution is left to stir again overnight. The reaction mixture is acidifed with 30 mL 3\(M\) sulfuric acid. The organic layer was separated, washed with deionized water, and the organic layer dried over Na\({}_{2}\)SO\({}_{4}\). The solvent was evaporated under reduced pressure, and subjected to radial chromatography. After recrystallization from cyclohexane, **4b** was obtained as reddish-brown crystals in 27% yield, mp 133-135 \({}^{\circ}\)C. **4b**: NMR. \({}^{1}\)H: 6 2.85 (2H, t, 7.6 Hz), 2.93 (2H, t, 7.6 Hz), 6.76 (s, 1H), 7.37-7.77 (4H, m), 15.68 (2H, bs). \({}^{13}\)C: 6 20.9, 22.7, 104.6, 118.4 (CF\({}_{3}\), q, \({}^{1}\)J\({}_{\text{C-F}}\) = 270 Hz), 125.9, 126.8, 127.3, 127.4, 128.2, 128.5, 128.6, 129.9, 133.9, 142.8, 177.0 (C-CF\({}_{3}\), q, \({}^{2}\)J\({}_{\text{C-F}}\) = 36 Hz), 182.2. \({}^{19}\)F (C\({}_{6}\)F ext. std. ): \(\delta\) -72.04 (s, 3F). Analysis calcd for C\({}_{14}\)H\({}_{11}\)F\({}_{3}\)O\({}_{3}\): C, 59.16, H, 3.90. Found: C, 58.99, H, 4.01. 2-trifluoroacetyl-1-tetralone (**4c**). This compound was obtained as off-white crystals, **4c**, in 53% yield, m.p. 50-52 \({}^{\circ}\)C lit [18] (m.p. 51-52 \({}^{\circ}\)C). **4c**: NMR: \({}^{1}\)H: \(\delta\) 2.75 (2H, t, 9.0 Hz), 2.88 (2H, t, 9.0 Hz), 7.16-7.87 (4H, m), 15.62 (1H, bs). \({}^{13}\)C: \(\delta\) 21.0, 27.8, 38.3, 103.7, 117.5 (CF\({}_{3}\), q, \({}^{1}\)J\({}_{\text{C-F}}\) = 285 Hz), 127.1, 127.3, 127.8, 127.9, 130.5, 133.4, 157.3, 174.8 (C-CF\({}_{3}\), q, \({}^{2}\)J\({}_{\text{C-F}}\) = 35 Hz), 185.0 \({}^{19}\)F (C\({}_{6}\)F ext. std. ): \(\delta\) -70.61 (s, 3F). HRMS (ESI+) calcd for C\({}_{12}\)H\({}_{9}\)F\({}_{3}\)O\({}_{2}\): 242.04470, found: 242.04436. 4,4,4-trifluoro-1-(1-hydroxynaphthyl)-1,3-butanedione (**5b**) [17]. A 100 mL RBF equipped with a magnetic stir bar is charged with 50 mL dry Et\({}_{2}\)O, 5 mL dry diisopropylamine (DIPA) and placed under N\({}_{2}\) at 0 \({}^{\circ}\)C. To this is added LDA (6.0 mL, 0.0120 mol) and stirred for fifteen minutes. Then, a solution of **5a** (0.740 g, 0.004 mol) in 15 mL dry Et\({}_{2}\)O is added dropwise slowly via syringe. After 8 h, ethyl trifluoroacetate (0.96 mL, 0.008 mol) is delivered dropwise slowly via syringe and the reaction mixture is stirred overnight and allowed to warm to rt. After 24 h, another equivalent of ethyl trifluoroacetate (0.46 mL, 0.004 mol) is added all at once.