19
NMR (300 MHz, CDCl3): δ ppm 7.74-7.68 (m, 4H), 7.64-7.61 (m, 2H), 7.53-7.43 (m, 3H). F NMR
(376 MHz, CDCl3): δ ppm -62.38 (s, 3F). 13C NMR (100.7 MHz, CDCl3): δ ppm 144.85, 139.90,
129.33 (q, J = 33.0 Hz), 129.13, 128.34, 127.56, 127.42, 125.84 (q, J = 3.7 Hz), 124.46 (q, J = 274.5
Hz). MS (EI): m/z (%) 222 (100). HRMS: Calculated for C13H9F3: 222.0656; Found [M]+, 222.0654.
4.3.2. 1-(Benzyloxy)-4-(trifluoromethyl)benzene (2c
Compound 2c was prepared following the general procedure in 39% yield, starting from (4-
(benzyloxy)phenyl)-(mesityl)iodonium tetrafluoroborate (258.1 mg, 0.5 mmol) prepared by procedure B.
1H NMR (300 MHz, CDCl3): δ ppm 7.56 (d, J = 8.7 Hz, 2H), 7.46-7.36 (m, 5H), 7.05 (d, J = 8.7 Hz,
2H), 5.12 (s, 2H). 19F NMR (376 MHz, CDCl3): δ ppm -61.47 (s, 3F). 13C NMR (100.7 MHz, CDCl3): δ
ppm 161.29 (d, J = 1.6 Hz), 136.33, 128.86, 128.41, 127.62, 127.07 (q, J = 3.7 Hz), 124.57 (q, J = 272.6
Hz), 123.21 (q, J = 32.9 Hz), 114.96, 70.27. MS (EI): m/z (%) 252 (100). HRMS: Calculated for
C14H11OF3: 252.0755; Found [M]+, 252.0754.
4.3.3. 1-Phenoxy-4-(trifluoromethyl)benzene (2d)
Compound 2d was prepared following the general procedure in 34% yield, starting from mesityl(4-
1
phenoxyphenyl)iodonium tetrafluoroborate (251.1 mg, 0.5 mmol) prepared by procedure B. H NMR
(300 MHz, CDCl3): δ ppm 7.58 (d, J = 8.4 Hz, 2H), 7.40 (t, J = 7.9 Hz, 2H), 7.20 (t, J = 7.5 Hz, 1H),
7.08-7.04 (m, 4H). 19F NMR (376 MHz, CDCl3): δ ppm -61.75 (s, 3F). 13C NMR (100.7 MHz, CDCl3):
δ ppm 160.73 (d, J = 1.5 Hz), 155.90, 130.27, 127.31 (q, J = 3.8 Hz), 125.02 (q, J = 33.5 Hz), 124.70,
124.41 (q, J = 272.0 Hz), 120.14, 118.04. MS (EI): m/z (%) 238 (100). HRMS: Calculated for
C13H9OF3: 238.0605; Found [M]+, 238.0601.
4.3.4. 2-(Trifluoromethyl)naphthalene (2e)
Compound 2e was prepared following the general procedure in 80% yield, starting from
1
mesityl(naphthalen-2-yl)iodonium tetrafluoroborate (230.0 mg, 0.5 mmol) prepared by procedure B. H
19
NMR (300 MHz, CDCl3): δ ppm 8.19-8.14 (m, 1H), 8.00-7.89 (m, 3H), 7.67-7.56 (m, 3H). F NMR
(376 MHz, CDCl3): δ ppm -62.26 (s, 3F). 13C NMR (100.7 MHz, CDCl3): δ ppm 134.55, 132.17,
128.98, 128.80, 128.05, 127.86, 127.70 (q, J = 32.4 Hz), 127.15, 125.68 (q, J = 4.5 Hz), 124.40 (q, J =
272.5 Hz), 121.43 (q, J = 3.4 Hz). MS (EI): m/z (%) 196 (100). HRMS: Calculated for C11H7F3:
196.0500; Found [M]+, 196.0504.
4.3.5. 1-Methyl-4-(trifluoromethyl)naphthalene (2f)
Compound 2f was prepared following the general procedure in 76% yield, starting from mesityl(4-
1
methylnaphthalen-1-yl)iodonium tetrafluoroborate (237.0 mg, 0.5 mmol) prepared by procedure B. H
NMR (300 MHz, CDCl3): δ ppm 8.30-8.27 (m, 1H), 8.11-8.08 (m, 1H), 7.79 (d, J = 7.5 Hz, 1H), 7.67-
7.63 (m, 2H), 7.34 (d, J = 7.5 Hz, 1H), 2.74 (s, 3H). 19F NMR (376 MHz, CDCl3): δ ppm -59.25 (s, 3F).
13C NMR (100.7 MHz, CDCl3): δ ppm 139.72, 133.18, 129.17, 127.31, 126.53, 125.18 (q, J = 273.3
Hz), 125.05, 124.91, 124.87, 124.58 (q, J = 6.0 Hz), 124.56 (q, J = 30.1 Hz), 19.82. MS (EI): m/z (%)
210 (100). HRMS: Calculated for C12H9F3: 210.0656; Found [M]+, 210.0651.
4.3.6. Methyl 2-(trifluoromethyl)benzoate (2g)
Compound 2g was prepared following the general procedure in 56% yield, starting from mesityl[2-
(methoxycarbonyl)phenyl]iodonium trifluoromethanesulfonate (265.2 mg, 0.5 mmol) prepared by
1
procedure A. H NMR (300 MHz, CDCl3): δ ppm 8.00-7.73 (m, 2H), 7.62-7.59 (m, 2H), 3.94 (s, 3H).
19F NMR (376 MHz, CDCl3): δ ppm -59.76 (s, 3F). 13C NMR (100.7 MHz, CDCl3): δ ppm 167.44,
131.85 (d, J = 2.2 Hz), 131.33, 130.30, 128.88 (q, J = 32.6 Hz), 126.81 (q, J = 5.6 Hz), 123.47 (q, J =
273.9 Hz), 52.98. MS (EI): m/z (%) 204 (100). HRMS: Calculated for C9H7O2F3: 204.0398; Found
[M]+, 204.0399.
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