7
1
1
pale yellow oil; Yield = 94.4%; H N
A
M
C
R
C
(
E
50
P
0
T
M
E
H
D
z, MANUpa
S
le
C
y
R
ell
I
o
P
w oil; Yield = 79.5%; H NMR (500 MHz,
T
CDCl ): δ 7.59 - 7.46 (m, 3H), 7.23 (d, J = 7.3 Hz, 2H), 7.06 -
.94 (m, 4H), 5.44 (s, 2H); C NMR (125 MHz, CDCl ): δ 174.2
q, J = 33.3 Hz), 162.8 (d, JC-F = 247.5 Hz), 143.8, 138.2,
31.0, 129.8 (d, JC-F = 8.75 Hz), 129.7 (d, JC-F = 3.75 Hz),
29.4, 129.1, 124.5, 116.0 (d, J = 21.25 Hz), 116.1 (q, J
88.8 Hz), 51.6; F NMR (470 MHz, CDCl ): δ -74.1 (s, 3F), -
12.4 (s, 1F); IR (KBr) v: 3670, 2927, 1720, 1607, 1558, 1513,
CDCl ): δ 7.60 - 7.48 (m, 3H), 7.38 (d, J = 6.8 Hz, 2H), 7.31 -
7.13 (m, 2H), 6.95 (t, J = 8.7 Hz, 1H), 5.57 (s, 2H); C NMR
3
3
13
13
6
(
1
1
2
3
2
1’
2
1’
(125 MHz, CDCl ): δ 174.2 (q, J = 36.7 Hz), 161.7 (d, J
=
C-F
3
C-F
C-F
4’
3’
3’
251.25 Hz), 144.1, 137.7, 135.8 (d, JC-F = 5.0 Hz), 131.4 (d,
JC-F = 10.0 Hz), 130.9, 129.4, 129.0, 125.7 (d, J = 3.75 Hz),
124.5, 119.6 (d, JC-F = 11.25 Hz), 116.6 (q, J = 292.5 Hz),
114.4 (d, JC-F = 21.25 Hz), 44.0; F NMR (470 MHz, CDCl ): δ
2’
1
3’’
2’
=
C-F
C-F
C-F
19
4’
1
3
C-F
2
’’
19
1
3
1
6
488, 1458, 1276, 1155, 1096, 1014, 936, 907, 841, 792, 735,
97, 558, 523, 492 cm ; HRMS (EI-TOF) calculated [M] for
-74.1 (s, 3F), -111.9 (s, 1F); IR (KBr) v: 3426, 2926, 2853, 1720,
-1
+
1608, 1582, 1488, 1456, 1359, 1274, 1154, 1092, 1013, 920, 861,
-
1
+
C H F N O:349.0839, found:349.0837 .
792, 741, 696, 565, 519 cm ; HRMS (EI-TOF) calculated [M]
17
11
4
3
for C H ClF N O: 385.0419, found: 385.0417.
17
10
4
3
5
2
.4.4.
1-(1-(4-bromobenzyl)-4-phenyl-1H-1,2,3-triazol-5-yl)-
,2,2-trifluoroethan-1-one (3da)
5.4.9. 1-(1-(2,6-difluorobenzyl)-4-phenyl-1H-1,2,3-triazol-5-yl)-
1
2,2,2-trifluoroethan-1-one (3ia)
pale yellow oil; Yield = 93.9%; H NMR (500 MHz,
CDCl ): δ 7.59 - 7.39 (m, 5H), 7.23 (d, J = 7.5 Hz, 2H), 6.92 (d, J
1
pale yellow oil; Yield = 79.7%; H NMR (500 MHz,
3
13
=
8.2 Hz, 2H), 5.42 (s, 2H); C NMR (125 MHz, CDCl ): δ
74.2 (q, J = 37.5 Hz), 143.9, 138.2, 132.9, 132.2, 131.1,
29.5, 129.4, 129.1, 124.3, 123.0, 116.1 (q, J = 288.3 Hz),
1.6; F NMR (470 MHz, CDCl ): δ -74.2 (s, 3F); IR (KBr) v:
670, 3429, 3140, 2924, 2853, 1718, 1591, 1488, 1457, 1155,
011, 937, 907, 697, 542 cm ; HRMS (EI-TOF) calculated [M]
CDCl ): δ 7.55 (d, J = 5.0 Hz, 3H), 7.36 (d, J = 45.0 Hz, 3H),
3
3
2
13
2
1
1
5
3
1
6.86 (s, 2H); C NMR (125 MHz, CDCl ): δ 174.1 (q, J
=
C-F
3
C-F
1
1’
37.1 Hz), 161.3 (dd, J =252.0, 6.8Hz), 144.2, 137.8, 131.5 (t,
C-F
3’ 1
C-F
19
JC-F = 10.6Hz), 130.9, 129.3, 129.0, 124.3, 116.2 (q, J
=
3
C-F
2
’
2’’
288.8 Hz), 111.6 (dd, J =20.3,4.3 Hz), 109.8 (t, JC-F = 18.1
C-F
-
1
+
19
Hz), 40.5; F NMR (470 MHz, CDCl ): δ -74.1 (s, 3F), -113.9 (s,
3
for C H BrF N O: 409.0038, found: 409.0036.
2F); IR (KBr) v: 3071, 1723, 1629, 1598, 1559, 1488, 1475,
17
11
3
3
1
5
3
361, 1301, 1276, 1238, 1202, 1159, 1094, 1024, 929, 797, 697,
5
2
.4.5. 1-(1-(3,5-dimethylbenzyl)-4-phenyl-1H-1,2,3-triazol-5-yl)-
,2,2-trifluoroethan-1-one (3ea)
-
1
+
22 cm ; HRMS (EI-TOF) calculated [M] for C H F N O:
17
10
5
3
67.0744, found: 367.0745.
1
pale yellow oil; Yield = 86.6%; H NMR (500 MHz,
5
.4.10. 2,2,2-trifluoro-1-(1-(naphthalen-1-ylmethyl)-4-phenyl-
CDCl ): δ 7.59 - 7.46 (m, 3H), 7.24 (d, J = 7.6 Hz, 2H), 6.92 (s,
1
MHz, CDCl ): δ 174.2 (q, J = 36.7 Hz), 143.9, 138.7, 138.1,
1
2
3
1
3
13
1H-1,2,3-triazol-5-yl)ethan-1-one (3ja)
H), 6.63 (s, 2H), 5.39 (s, 2H), 2.23 (s, 6H); C NMR (125
2
1
pale yellow oil; Yield = 88.4%; H NMR (500 MHz,
3
C-F
1
33.7, 130.9, 130.4, 129.5, 128.9, 125.6, 124.6, 116.2 (q, J
88.8 Hz), 52.3, 21.2; F NMR (470 MHz, CDCl ): δ -74.1 (s,
=
CDCl ): δ 7.83 - 7.69 (m, 3H), 7.60 - 7.41 (m, 6H), 7.29 - 7.18
C-F
3
19
13
(m, 3H), 5.63 (s, 2H); C NMR (125 MHz, CDCl ): δ 174.2 (q,
3
3
2
F); IR (KBr) v: 3679, 3155, 2922, 1719, 1606, 1556, 1488,
JC-F = 36.7 Hz), 144.1, 138.2, 133.1, 133.1, 131.3, 131.0, 129.5,
-
1
457, 1274, 1200, 1155, 1014, 911, 777, 696, 532, 419 cm ;
129.1, 129.0, 128.0, 127.8, 127.2, 126.8, 126.8, 124.9, 124.6,
116.2 (q, J = 288.8 Hz), 52.5; F NMR (470 MHz, CDCl ): δ
+
1
19
HRMS (EI-TOF) calculated [M] for C H F N O: 359.1245,
19
16
3
3
C
-
F
3
found: 359.1244 .
-74.0 (s, 3F); IR (KBr) v: 3676, 3167, 2946, 1893, 1719, 1600,
-1
1
513, 1488, 1458, 1276, 1188, 939, 699, 528 cm ; HRMS (EI-
5
.4.6. 1-(1-(3,5-bis(trifluoromethyl)benzyl)-4-phenyl-1H-1,2,3-
+
TOF) calculated [M] for C H F N O: 381.1089, found:
21
14
3
3
triazol-5-yl)-2,2,2-trifluoroethan-1-one (3fa)
3
81.1090.
1
pale yellow oil; Yield = 79.7%; H NMR (500 MHz,
5
.4.11.
2,2,2-trifluoro-1-(1-(naphthalen-2-ylmethyl)-4-phenyl-
CDCl ): δ 7.82 (s, 1H), 7.63 - 7.46 (m, 5H), 7.24 - 7.21 (d, J =
3
13
1H-1,2,3-triazol-5-yl)ethan-1-one (3ka)
7
.3 Hz, 2H), 5.60 (s, 2H); C NMR (125 MHz, CDCl ): δ 174.1
3
2 1’
1
(q, J = 37.1 Hz), 143.9, 138.4, 135.9, 132.5 (q, J = 33.75
pale yellow oil; Yield = 84.1%; H NMR (500 MHz,
C-F
C-F
2’
Hz), 131.4, 129.3, 129.2, 128.6, 123.9 (d, JC-F = 36.25 Hz),
CDCl ): δ 7.93 - 7.79 (m, 3H), 7.57 - 7.14 (m, 8H), 6.82 (d, J =
3
1
19
13
1
23.0 (m), 121.6, 116.0 (q, J = 288.8 Hz), 51.3; F NMR
7.1 Hz, 1H), 5.97 (s, 2H); C NMR (125 MHz, CDCl ): δ 174.2
C-F
3
2
(470 MHz, CDCl ): δ -63.1 (s, 6F), -74.3 (s, 3F); IR (KBr) v:
(q, J = 36.7 Hz), 144.3, 138.2, 133.7, 130.9, 130.5, 129.6,
3
C-F
3
6
670, 3429, 3140, 1718, 1591, 1457, 1383, 1279, 1133, 911, 699,
129.4, 129.3, 129.0, 129.0, 127.1, 126.8, 126.3, 125.1, 124.6,
-
1
+
1
19
82, 537 cm ; HRMS (EI-TOF) calculated [M] for C H
122.5, 116.2 (q, J = 288.8 Hz), 50.3; F NMR (470 MHz,
19
10
C-F
F N O: 467.0680, found: 467.0679.
CDCl ): δ -74.0 (s, 3F); IR (KBr) v: 3623, 3051, 2960, 2927,
9
3
3
2
855, 1696, 1614, 1568, 1490, 1456, 1322, 1182, 1158, 1132,
5
.4.7. 1-(1-(3,5-di-tert-butylbenzyl)-4-phenyl-1H-1,2,3-triazol-5-
-
1
+
1105, 944, 774, 697, 545 cm ; HRMS (EI-TOF) calculated [M]
yl)-2,2,2-trifluoroethan-1-one (3ga)
for C H F N O: 381.1089, found: 381.1090.
21
14
3
3
1
pale yellow oil; Yield = 86.4%; H NMR (500 MHz,
5
.4.12.
2,2,2-trifluoro-1-(1-octyl-4-phenyl-1H-1,2,3-triazol-5-
CDCl ): δ 7.59 - 7.48 (m, 3H), 7.36 (s, 1H), 7.28 (d, J = 7.8 Hz,
2
NMR (125 MHz, CDCl ): δ 174.3 (q, J = 36.7 Hz), 151.7,
3
13
yl)ethan-1-one (3la)
H), 6.92 (s, 2H), 5.47 (s, 2H), 1.30 (s, 2H), 1.25 (s, 12H); C
2
1
pale yellow oil; Yield = 89.9%; H NMR (500 MHz,
3
C-F
1
43.7, 138.2, 133.1, 130.8, 129.6, 128.9, 124.9, 122.8, 122.4,
CDCl ): δ 7.57 (t, J = 7.5 Hz , 3H), 7.36 (d, J = 5.0 Hz , 2H),
3
1
19
116.2 (q, J = 288.8 Hz), 53.0, 34.8, 31.3; F NMR (470 MHz,
5.28 (s, 2H), 4.27 (t, J = 5.0 Hz , 2H), 1.55 (s, 4H), 1.19 (s, 8H),
C-F
1
3
CDCl ): δ -74.1 (s, 3F); IR (KBr) v: 3670, 3148, 2963, 1719,
1
6
0.86 (t, J = 7.5 Hz , 3H); C NMR (125 MHz, CDCl ): δ 174.2
3
3
2
640, 1557, 1458, 1363, 1249, 1201, 1158, 1095, 949, 914, 778,
(q, J = 36.3 Hz), 143.7, 137.9, 130.8, 129.7, 129.3, 129.1,
C-F
-
1
+
1
96, 526 cm ; HRMS (EI-TOF) calculated [M] for
128.6, 124.8, 116.2 (q, J = 289.2 Hz), 53.4, 48.5, 31.6, 29.8,
C-F
1
9
C H F N O: 443.2184, found: 443.2182.
28.9, 28.7, 26.3, 22.5, 14.0; F NMR (470 MHz, CDCl ): δ -74.1
25
28
3
3
3
(
1
s, 3F); IR (KBr) v: 3735, 2922, 2851, 1743, 1732, 1715, 1659,
5
5
.4.8. 1-(1-(2-chloro-6-fluorobenzyl)-4-phenyl-1H-1,2,3-triazol-
-yl)-2,2,2-trifluoroethan-1-one (3ha)
-1
597, 1564, 1494, 1397, 1261, 1179, 1033, 763, 695, 503 cm ;
+
HRMS (EI-TOF) calculated [M] for C H F N O: 353.1715,
18
22
3
3
found: 353.1713.