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YANG ET AL.
(C39H45N3O4Pd): C, 64.50; H, 6.25; N, 5.79%. Found: C,
64.21; H, 6.53; N, 6.06%.
and found 618.2259; calcd for C35H45N4O2Pd
[M + CH3CN–OAc−]+ 659.2577 and found 659.2520.
Anal. Calcd for [(SIPr)Pd (pyridine-2-carboxylate)(OAc)]
(C35H45N3O4Pd): C, 61.99; H, 6.69; N, 6.20%. Found: C,
62.33; H, 6.98; N, 6.48%.
4.5 | [(IPr)Pd (isoquinoline-1-carboxylate)
(OAc)] (3c)
The procedure yielded 305 mg (84%) of the pure complex
3c as a yellow powder. H NMR (CDCl3, 600 MHz) δ
4.7 | [(SIPr)Pd (quinoline-2-carboxylate)
(OAc)] (3e)
1
(ppm) = 9.78 (d, J = 8.4 Hz, 1H, CH-isoquinoline),
7.69–7.64 (m, 3H, CH-isoquinoline), 7.61–7.57 (m, 2H,
CH-isoquinoline), 7.49 (t, J = 7.8 Hz, 2H, p-CH-aniline),
7.35 (d, J = 7.8 Hz, 4H, m-CH-aniline), 7.18 (s, 2H,
NCH=CHN), 2.91 (sept, J = 6.6 Hz, 4H, CH (CH3)2), 1.86
(s, 3H, CH3COO−), 1.43 (d, J = 7.2 Hz, 12H, CH (CH3)2),
1.14 (d, J = 7.2 Hz, 12H, CH (CH3)2). 13C NMR (CDCl3,
150 MHz) δ (ppm) = 176.82 (CH3COO−), 173.24
The procedure yielded 302 mg (83%) of the pure complex
3e as a yellow powder. H NMR (CDCl3, 600 MHz) δ
1
(ppm) = 8.19 (d, J = 8.4 Hz, 1H, CH-quinoline), 8.11 (d,
J = 9.0 Hz, 1H, CH-quinoline), 7.96 (d, J = 8.4 Hz, 1H,
CH-quinoline), 7.67 (dd, J = 7.8 Hz and 0.6 Hz, 1H, CH-
quinoline), 7.50–7.47 (m, 1H, CH-quinoline), 7.44–7.42
(m, 1H, CH-quinoline), 7.35 (t, J = 7.8 Hz, 2H, p-CH-ani-
line), 7.27 (d, J = 7.8 Hz, 4H, m-CH-aniline), 4.11 (s, 2H,
NCH=CHN), 3.44 (sept, J = 6.6 Hz, 4H, CH (CH3)2), 1.57
(d, J = 7.2 Hz, 12H, CH (CH3)2), 1.40 (s, 3H, CH3COO−),
1.31 (d, J = 7.2 Hz, 12H, CH (CH3)2). 13C NMR (CDCl3,
(Isoquinoline-COO−),
(Cisoquinoline), 146.44 (N-Caniline), 138.48 (Cisoquinoline),
137.59 (Cisoquinoline), 134.71 (o-Caniline), 131.80
159.28
(Ccarbene),
148.67
(Cisoquinoline), 130.31 (p-Caniline), 129.08 (Cisoquinoline),
127.78 (Cisoquinoline), 127.26 (Cisoquinoline), 126.36
(Cisoquinoline), 125.03 (NCH=CHN), 124.68 (Cisoquinoline),
124.05 (m-Caniline), 28.54 (CH (CH3)2), 26.08 (CH (CH3)2),
23.61 (CH3COO−), 22.77 (CH (CH3)2). HR-MS (ESI):
calcd for C37H42N3O2Pd [M–OAc−]+ 666.2312 and found
666.2266; calcd for C39H45N4O2Pd [M + CH3CN–OAc−]+
707.2577 and found 707.2533. Anal. Calcd for [(IPr)Pd
(isoquinoline-1-carboxylate)(OAc)] (C39H45N3O4Pd): C,
64.50; H, 6.25; N, 5.79%. Found: C, 64.77; H, 6.01; N,
5.52%.
150 MHz)
δ
(ppm)
173.10
=
185.21 (Ccarbene), 176.14
(CH3COO−),
(Quinoline-COO−),
152.59
(Cquinoline), 147.23 (N-Caniline), 145.96 (Cquinoline), 139.53
(Cquinoline), 134.52 (o-Caniline), 130.35 (Cquinoline), 129.81
(Cquinoline), 129.28 (p-Caniline), 127.96 (Cquinoline), 127.68
(Cquinoline), 126.16 (Cquinoline), 124.57 (m-Caniline), 122.02
(Cquinoline), 53.73 (NCH2CH2N), 28.75 (CH (CH3)2), 26.39
(CH (CH3)2), 23.64 (CH (CH3)2), 22.89 (CH3COO−). HR-
MS (ESI): calcd for C37H44N3O2Pd [M–OAc−]+ 668.2468
and found 668.2410; calcd for C39H47N4O2Pd
[M + CH3CN–OAc−]+ 709.2734 and found 709.2681.
Anal. Calcd for [(SIPr)Pd (quinoline-2-carboxylate)
(OAc)] (C39H47N3O4Pd): C, 64.32; H, 6.51; N, 5.77%.
Found: C, 64.66; H, 6.80; N, 6.04%.
4.6 | [(SIPr)Pd (pyridine-2-carboxylate)
(OAc)] (3d)
The procedure yielded 300 mg (88%) of the pure complex
1
3d as a yellow powder. H NMR (CDCl3, 600 MHz) δ
4.8 | [(SIPr)Pd (isoquinoline-
1-carboxylate)(OAc)] (3f)
(ppm) = 7.80 (d, J = 7.8 Hz, 1H, CH-pyridyl), 7.76 (d,
J = 7.8 Hz, 1H, CH-pyridyl), 7.74 (t, J = 6.6 Hz, 1H, CH-
pyridyl), 7.40 (t, J = 7.8 Hz, 2H, p-CH-aniline), 7.29 (d,
J = 7.8 Hz, 4H, m-CH-aniline), 7.24 (t, J = 6.6 Hz, 1H,
CH-pyridyl), 4.09 (s, 2H, NCH2CH2N), 3.39 (sept,
J = 6.6 Hz, 4H, CH (CH3)2), 1.76 (s, 3H, CH3COO−), 1.45
(d, J = 6.6 Hz, 12H, CH (CH3)2), 1.27 (d, J = 7.2 Hz, 12H,
CH (CH3)2). 13C NMR (CDCl3, 150 MHz) δ (ppm) = 188.19
(Ccarbene), 176.02 (CH3COO−), 172.77 (pyridyl-COO−),
150.79 (Cpyridyl), 147.42 (Cpyridyl), 146.66 (N-Caniline),
139.07 (Cpyridyl), 134.70 (o-Caniline), 129.43 (p-Caniline),
126.53 (Cpyridyl), 126.10 (Cpyridyl), 124.55 (m-Caniline),
53.66 (NCH2CH2N), 28.54 (CH (CH3)2), 26.57
(CH3COO−), 26.34 (CH (CH3)2), 23.62 (CH (CH3)2). HR-
MS (ESI): calcd for C33H42N3O2Pd [M–OAc−]+ 618.2312
The procedure yielded 295 mg (81%) of the pure complex
1
3f as a yellow powder. H NMR (CDCl3, 600 MHz) δ
(ppm) = 9.78 (d, J = 8.4 Hz, 1H, CH-isoquinoline), 7.73
(d, J = 6.0 Hz, 1H, CH-isoquinoline), 7.69–7.65 (m, 2H,
CH-isoquinoline), 7.61–7.58 (m, 2H, CH-isoquinoline),
7.38 (t, J = 7.8 Hz, 2H, p-CH-aniline), 7.28 (d, J = 7.8 Hz,
4H, m-CH-aniline), 4.12 (s, 4H, NCH2CH2N), 3.47 (sept,
J = 6.6 Hz, 4H, CH (CH3)2), 1.82 (s, 3H, CH3COO−), 1.50
(d, J = 6.6 Hz, 12H, CH (CH3)2), 1.29 (d, J = 7.2 Hz, 12H,
CH (CH3)2). 13C NMR (CDCl3, 150 MHz) δ (ppm) = 189.19
(Ccarbene), 175.83 (CH3COO−), 173.13 (Isoquinoline-
COO−), 148.52 (Cisoquinoline), 147.48 (N-Caniline), 137.60
(Cisoquinoline), 134.88 (o-Caniline), 131.75 (Cisoquinoline),