1-Ethyl-2-pyridyl-3-methylimidazolium bis(trifluoromethane-
sulfonyl)amide (3d). Pale-yellow liquid, yield: 90%. H NMR:
for C17H19F9N4O4S2 (578.07): C, 35.30; H, 3.31; N 9.69. Found: C,
35.14; H, 3.32; N, 9.57.
1
d 8.76–8.84 (m, 1H), 8.00–8.05 (m, 1H), 7.85–7.92 (m, 1H), 7.58
(d, 1H, J = 2.1 Hz), 7.43 (d, 1H, J = 1.2 Hz), 7.14–7.21 (m, 1H),
4.14 (q, 2H, J = 7.4 Hz), 3.80 (s, 3H), 1.41 (t, 3H, J = 7.3 Hz);
13C NMR: d 151.1, 142.8, 141.9, 138.3, 127.4, 126.9, 124.0, 121.5,
121.0 (q, J = 319.2 Hz), 44.9, 36.4, 15.1; 19F NMR: d −79.8 (s,
6F); MS (solid probe) (EI) m/z (%) 188 (M+, 100), Anal. Calcd
for C13H14F6N4O4S2 (468.04): C, 33.33; H, 3.01; N 11.96. Found:
C, 33.34; H, 3.03; N, 11.70.
1-Butyl-2-pyridyl-3-ethylimidazolium bis(trifluoromethanesul-
fonyl)amide (3i). Pale-yellow liquid, yield: 92%. 1H NMR: d
8.94–8.96 (m, 1H), 8.19–8.24 (m, 1H), 8.06–8.09 (m, 1H), 7.93
(d, 2H, J = 1.2 Hz), 7.77–7.82 (m, 1H), 4.26–4.35 (m, 4H), 1.81
(quintet, 2H, J = 7.4 Hz), 1.46 (t, 3H, J = 7.2 Hz), 1.26 (sextet,
2H, J = 7.5 Hz), 0.81 (t, 3H, J = 7.3 Hz); 13C NMR: d 152.1,
143.3, 142.3, 139.1, 128.0, 127.8, 123.6, 123.0, 121.0 (q, J = 319.4
Hz), 49.6, 45.3, 32.6, 19.9, 15.5, 13.5; 19F NMR: d −79.8 (s, 6F);
MS (solid probe) (EI) m/z (%) 230 (M+, 100), Anal. Calcd for
C16H20F6N4O4S2 (510.08): C, 37.65; H, 3.95; N 10.98. Found: C,
37.57; H, 3.91; N, 11.12.
1-Propyl-2-pyridyl-3-methylimidazolium bis(trifluoromethane-
1
sulfonyl)amide (3e). Pale-yellow liquid, yield: 87%. H NMR:
d 8.92–8.94 (m, 1H), 8.17–8.23 (m, 1H), 8.05–8.08 (m, 1H), 7.87
(d, 1H, J = 1.7 Hz), 7.83 (d, 1H, J = 1.2 Hz), 7.74–7.79 (m, 1H),
4.29 (t, 2H, J = 7.3 Hz), 3.98(s, 3H), 1.84 (sextet, 2H, J = 7.3
Hz), 0.84 (t, 3H, J = 7.3 Hz); 13C NMR: d 151.9, 143.2, 142.2,
139.0, 128.1, 127.7, 124.9, 123.3, 121.0 (q, J = 319.4 Hz), 51.4,
36.7, 23.9, 10.7; 19F NMR: d −79.8 (s, 6F); MS (solid probe) (EI)
m/z (%) 202 (M+, 100), Anal. Calcd for C14H16F6N4O4S2 (482.05):
C, 34.86; H, 3.34; N 11.61. Found: C, 34.59; H, 3.26; N, 11.54.
1-Butyl-2-pyridyl-3-propylimidazolium bis(trifluoromethanesul-
fonyl)amide (3j). Colorless solid, yield: 86%. H NMR: d 8.95–
1
8.98 (m, 1H), 8.21–8.26 (m, 1H), 8.08–8.11 (m, 1H), 7.96 (d, 2H,
J = 1.1 Hz), 7.79–7.83 (m, 1H), 4.25–4.33 (m, 4H), 1.77–1.89 (m,
4H), 1.26 (sextet, 2H, J = 7.4 Hz), 0.78–0.87 (m, 6H); 13C NMR: d
152.1, 143.3, 139.1, 128.1, 127.8, 123.5, 123.4, 121.0 (q, J = 319.4
Hz), 51.3, 49.6, 32.5, 23.9, 19.8, 13.4, 10.7; 19F NMR: d −79.8 (s,
6F); MS (solid probe) (EI) m/z (%) 244 (M+, 100), Anal. Calcd
for C17H22F6N4O4S2 (524.1): C, 38.93; H, 4.23; N 10.68. Found: C,
38.95; H, 4.18; N, 10.68.
1-Butyl-2-pyridyl-3-methylimidazolium bis(trifluoromethanesul-
fonyl)amide (3f). Pale-yellow liquid, yield: 93%. 1H NMR: d 8.95
(d, 1H, J = 4.6 Hz), 8.20–8.25 (m, 1H), 8.10 (d, 1H, J = 7.8 Hz),
7.92 (d, 1H, J = 2.0 Hz), 7.87 (d, 1H, J = 1.9 Hz), 7.77–7.81 (m,
1H), 4.35 (t, 2H, J = 7.4 Hz), 4.01 (s, 3H), 1.82 (quintet, 2H, J =
7.4 Hz), 1.27 (sextet, 2H, J = 7.5 Hz), 0.82 (t, 3H, J = 7.4 Hz);
13C NMR: d 152.0, 143.3, 142.3, 139.1, 128.2, 127.8, 125.0, 123.4,
121.0 (q, J = 319.4 Hz), 49.8, 36.8, 32.7, 19.9, 13.5; 19F NMR: d
−79.8 (s, 6F); MS (solid probe) (EI) m/z (%) 216 (M+, 100), Anal.
Calcd for C15H18F6N4O4S2 (496.07): C, 36.29; H, 3.65; N 11.29.
Found: C, 35.90; H, 3.64; N, 11.13.
1-(4,4,4-Triflurobutyl)-2-pyridyl-3-butylimidazolium bis(tri-
fluoromethanesulfonyl) amide (3k). Pale-yellow liquid, yield:
83%. 1H NMR: d 8.94–8.96 (m, 1H), 8.20–8.25 (m, 1H), 8.09–8.12
(m, 1H), 7.98 (d, 2H, J = 10.96 Hz), 7.78–7.82 (m, 1H), 4.42 (t,
2H, J = 7.1 Hz), 4.30 (t, 2H, J = 7.0 Hz), 2.15–2.34 (m, 4H), 1.80
(quintet, 2H, J = 7.4 Hz), 1.25 (sextet, 2H, J = 7.3 Hz), 0.79 (t,
3H, J = 7.3 Hz); 13C NMR: d 152.1, 143.6, 142.0, 139.2, 128.2,
127.9 (q, J = 273.8 Hz), 127.8, 127.2, 123.7, 122.4, 120.9 (q, J =
319.2 Hz), 49.6, 48.4, 32.4, 30.8 (q, J = 29.5 Hz), 23.5 (q, J = 3.3
Hz), 19.8, 13.4; 19F NMR: d −66.9 (t, 3F, J = 10.4 Hz), −79.9 (s,
6F); MS (solid probe) (EI) m/z (%) 312 (M+, 100), Anal. Calcd
for C18H21F9N4O4S2 (592.09): C, 36.49; H, 3.57; N 9.46. Found:
C, 36.50; H, 3.60; N, 9.66.
1-Hexyl-2-pyridyl-3-methylimidazolium bis(trifluoromethane-
1
sulfonyl)amide (3g). Pale-yellow liquid, yield: 92%. H NMR:
d 8.94–8.96 (m, 1H), 8.19–8.25 (m, 1H), 8.08–8.11 (m, 1H), 7.92
(d, 1H, J = 2.1 Hz), 7.86 (d, 1H, J = 2.0 Hz), 7.77–7.85 (m, 1H),
4.35 (t, 2H, J = 7.4 Hz), 4.00 (s, 3H), 1.83 (quintet, 2H, J = 7.3
Hz), 1.16–1.30 (m, 6H), 0.81 (t, 3H, J = 7.0 Hz); 13C NMR: d
152.0, 143.6, 142.3, 139.1, 128.1, 127.3, 125.0, 123.4, 121.0 (q, J
= 319.4 Hz), 50.0, 36.8, 31.6, 30.6, 26.3, 22.9, 14.0; 19F NMR: d
−79.8 (s, 6F); MS (solid probe) (EI) m/z (%) 244 (M+, 100), Anal.
Calcd for C17H22F6N4O4S2 (524.1): C, 38.93; H, 4.23; N 10.68.
Found: C, 39.09; H, 4.24; N, 10.83.
1-Hexyl-2-pyridyl-3-butylimidazolium bis(trifluoromethanesul-
fonyl)amide (3l). Pale-yellow liquid, yield: 92%. 1H NMR: d
8.95–8.97 (m, 1H), 8.20–8.26 (m, 1H), 8.08–8.11 (m, 1H), 7.95
(s, 2H), 7.78–7.83 (m, 1H), 4.30 (t, 4H, J = 7.4 Hz), 1.75–1.87 (m,
4H), 1.15–1.32 (m, 8H), 0.78–0.83 (m, 6H); 13C NMR: d 152.2,
143.5, 142.4, 139.2, 128.2, 127.9, 123.6, 123.5, 121.0 (q, J = 319.5
Hz), 49.9, 49.7, 32.6, 31.6, 30.5, 26.3, 22.9, 19.9, 14.0, 13.5; 19F
NMR: d −79.8 (s, 6F); MS (solid probe) (EI) m/z (%) 286 (M+,
100), Anal. Calcd for C20H28F6N4O4S2 (566.15): C, 42.40; H, 4.98;
N 9.89. Found: C, 41.73; H, 4.83 N, 9.78.
1-(4,4,4-Triflurobutyl)-2-pyridyl-3-propylimidazolium bis(tri-
fluoromethanesulfonyl) amide (3h). Pale-yellow liquid, yield:
1
85%. H NMR: d 8.89–8.91 (m, 1H), 8.13–8.17 (m, 1H), 8.02–
Palladium(II) [1-butyl-2-pyridyl-3-methylimidazolium
bis(trifluoromethanesulfonyl)amide] dichloride (4)
8.05 (m, 1H), 7.89 (d, 1H, J = 2.1 Hz), 7.85 (d, 1H, J = 2.1 Hz),
7.72–7.77 (m, 1H), 4.36 (t, 2H, J = 7.4 Hz), 4.21 (t, 2H, J = 7.3
Hz), 2.08–2.25 (m, 4H), 1.81 (sextet, 2H, J = 7.3 Hz), 0.81 (t,
3H, J = 7.4 Hz); 13C NMR: d 152.1, 143.7, 142.0, 139.1, 128.1,
127.8 (q, J = 273.8 Hz), 127.8, 127.2, 123.7, 123.4, 120.8 (q, J =
318.9 Hz), 51.4, 48.4, 30.8 (q, J = 29.5 Hz), 23.8, 23.5 (q, J =
3.3 Hz), 10.6; 19F NMR: d −66.9 (t, 3F, J = 10.4 Hz), −79.9 (s,
6F); MS (solid probe) (EI) m/z (%) 298 (M+, 100), Anal. Calcd
PdCl2 (0.035 g, 0.2 mmol) was added to a stirred solution of 3f
(0.199 g, 0.4 mmol) in methanol (10 ml). The mixture was stirred
for 12 h at 25 ◦C. Slow evaporation of the resulting solution gave
rise to pale-yellow crystals. Yield: (0.21 g, 90%). 1H NMR: d 9.31
(s, 2H), 8.50–8.55 (m, 2H), 8.36 (d, 2H, J = 7.7 Hz), 8.29 (d, 2H,
J = 2.0 Hz), 8.20 (s, 2H), 8.03–8.12 (m, 2H), 4.53 (t, 4H, J = 7.3
676 | Org. Biomol. Chem., 2007, 5, 671–678
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The Royal Society of Chemistry 2007
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