ACCEPTED MANUSCRIPT
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(E)-1,1,1-trifluoro-4-(2-methoxyphenyl)but-3-en-2-one (1f)21: H NMR (400 MHz, CDCl3) δ 8.18 (d, J = 16.1 Hz,
1H), 7.49 (d, J = 7.7 Hz, 1H), 7.38-7.34 (m, 1H), 7.04 (d, J = 16.1 Hz, 1H), 6.92-6.89 (m, 1H), 6.86 (d, J = 8.4 Hz, 1H),
3.83 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 180.5 (q, 2JC-F = 35.0 Hz), 159.6, 145.8, 133.8, 130.2, 122.3, 120.9, 117.0,
116.6 (q, 1JC-F = 289.0 Hz), 111.4, 55.6. 19F NMR (376 MHz, CDCl3) δ -77.56.
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(E)-4-(4-chlorophenyl)-1,1,1-trifluorobut-3-en-2-one (1g)13: H NMR (400 MHz, CDCl3) δ 7.91 (d, J = 16.0 Hz,
1H), 7.57 (d, J = 8.0 Hz, 2H), 7.42 (d, J = 8.0 Hz, 2H), 6.98 (d, J = 16.0 Hz, 1H). 13C NMR (100 MHz, CDCl3) δ
179.9 (q, 2JC-F = 36.0 Hz), 148.5, 138.5, 131.8, 130.3, 129.6, 117.1, 116.3 (q, 1JC-F= 289.0 Hz). 19F NMR (376 MHz,
CDCl3) δ -77.67.
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(E)-4-(4-bromophenyl)-1,1,1-trifluorobut-3-en-2-one(1h)13: H NMR (400 MHz, CDCl3) δ 7.90 (d, J = 15.9 Hz,
1H), 7.60 (d, J = 8.3 Hz, 2H), 7.50 (d, J = 8.3 Hz, 2H), 7.00 (d, J = 15.9 Hz, 1H). 13C NMR (100 MHz, CDCl3) δ
180.0 (q, 2JC-F = 35.0 Hz), 148.6, 132.6, 132.2, 130.5, 127.0, 117.1, 116.3 (q, 1JC-F = 289.0 Hz). 19F NMR (376 MHz,
CDCl3) δ -77.65.
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(E)-1,1,1-trifluoro-4-(4-fluorophenyl)but-3-en-2-one (1i)15: H NMR (400 MHz, CDCl3) δ 7.93 (d, J = 15.9 Hz,
1H), 7.74 – 7.58 (m, 2H), 7.17-7.13 (m, 2H), 6.94 (d, J = 15.9 Hz, 1H). 13C NMR (100 MHz, CDCl3) δ 180.0 (q, 2JC-F
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= 35.0 Hz), 165.7 (q, JC-F = 253.0 Hz), 148.7, 131.4,129.7, 116.6 (q, JC-F = 22.0 Hz), 116.0 (q, JC-F = 3.0 Hz). 19F
NMR (376 MHz, CDCl3) δ -77.66, -105.61.
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(E)-1,1,1-trifluoro-4-(2-fluorophenyl)but-3-en-2-one (1j)15: H NMR (400 MHz, CDCl3) δ 8.01 (d, J = 16.2 Hz,
1H), 7.56 (t, J = 7.4 Hz, 1H), 7.41 (dd, J = 13.2, 6.5 Hz, 1H), 7.19 – 7.09 (m, 2H), 7.06 (d, J = 15.9 Hz, 1H). 13C
NMR (100 MHz, CDCl3) δ 180.3 163.5, 142.7, 133.8, 130.1, 124.8, 121.7, 119.0, 116.7, 116.5. 19F NMR (376 MHz,
CDCl3) δ -77.83, -112.02.
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(E)-4-(2-bromophenyl)-1,1,1-trifluorobut-3-en-2-one (1k)22: H NMR (400 MHz, CDCl3) δ 8.37 (d, J = 15.9 Hz,
1H), 7.73-7.66 (m, 2H), 7.41-7.33 (m, 2H), 6.96 (d, J = 15.9 Hz, 1H). 13C NMR (100 MHz, CDCl3) δ 182.1 (q, 2JC-F
=
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35.0 Hz), 160.9, 148.23, 133.9, 133.3, 133.0, 128.2, 127.9, 126.9, 123.5, 119.1 (q, JC-F = 289.0 Hz). 19F NMR (376
MHz, CDCl3) δ -77.49.
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(E)-1,1,1-trifluoro-4-(4-(trifluoromethyl)phenyl)but-3-en-2-one (1l)23: H NMR (400 MHz, CDCl3) δ 7.89 (d, J =
16.0 Hz, 1H), 7.68 (d, J = 8.2 Hz, 2H), 7.64 (d, J = 8.2 Hz, 2H), 7.00 (d, J = 16.0 Hz, 1H). 13C NMR (100 MHz,
CDCl3) δ179.8 (q, 2JC-F = 35.0 Hz), 147.9, 136.5, 133.5 (q, 2JC-F = 33.0 Hz), 129.3, 126.4, 123.5 (q, 1JC-F = 271.0 Hz),
118.9, 116.2 (q, 1JC-F = 289.0 Hz). 19F NMR (376 MHz, CDCl3) δ -63.14, -77.74.
(E)-1,1,1-trifluoro-4-(4-hydroxyphenyl)but-3-en-2-one (1m) : 1H NMR (400 MHz, CDCl3) δ 7.93 (d, J = 16.0 Hz,
1H), 7.57 (d, J = 8.4 Hz, 2H), 6.91-6.86 (m, 2H), 6.88 (d, J = 16.0 Hz, 1H), 5.67 (s, 1H). 13C NMR (100 MHz, CDCl3)
δ 180.4 (q, 2JC-F = 35.0 Hz), 159.9, 150.5, 131.8, 126.2, 116.6 (q, 1JC-F= 289.0 Hz), 116.4, 113.9. 19F NMR (376 MHz,
CDCl3) δ -77.49. IR (KBr) ν 2923, 1705, 1576, 1514, 1444, 1273, 1200, 1168, 1062, 831, 708. GC-MS (EI) calcd.
for C10H7F3O2 [M]+: 216.0, found: m/z 216.0.
(3E,5E)-1,1,1-trifluoro-6-phenylhexa-3,5-dien-2-one (1n)27: 1H NMR (400 MHz, CDCl3) δ 7.71 (dd, J = 14.8, 11.4
Hz, 1H), 7.50 (d, J = 6.0 Hz, 2H), 7.38 -7.37(m, 3H), 7.11 (d, J = 15.5 Hz, 1H), 6.95 (dd, J = 15.2, 11.4 Hz, 1H), 6.53
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(d, J = 15.2 Hz, 1H). 13C NMR (100 MHz, CDCl3) δ 180.0 (q, JC-F = 35.0 Hz), 150.0, 146.2, 135.3, 130.4, 129.1,
127.9, 125.9, 119.8, 116.5 (q, 1JC-F = 289.0 Hz). 19F NMR (376 MHz, CDCl3) δ -77.41.
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(E)-1,1,1-trifluoro-4-(furan-2-yl)but-3-en-2-one (1o)15: H NMR (400 MHz, CDCl3) δ 7.68 (d, J = 15.5 Hz, 1H),
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7.61 (s, 1H), 6.90 (s, 1H), 6.87 (d, J = 15.5 Hz, 1H), 6.58 (s, 1H). 13C NMR (100 MHz, CDCl3) δ 179.8 (q, JC-F
=
35.0 Hz), 150.6, 147.0, 134.8, 119.9, 116.4 (q, 1JC-F= 288.0 Hz), 113.9, 113.5. 19F NMR (376 MHz, CDCl3) δ -77.70.
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