Palladacycle-Catalyzed Carbonylation of Aryl Iodides or Bromides with Aryl Formates
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125.7, 121.5, 116.8.
White crystal; H NMR (400 MHz, CDCl3) δ: 8.16 (d,
J=8.8 Hz, 2H), 7.44-7.36 (m, 2H), 7.26 (t, J=7.4 Hz,
1H), 7.20 (d, J=8.1 Hz, 2H), 6.98 (d, J=8.9 Hz, 2H),
3.88 (s, 3H); 13C NMR (100 MHz, CDCl3) δ: 164.7,
163.8, 150.8, 132.1, 129.2, 125.5, 121.8, 121.8, 113.6,
55.3.
3-Methylbenzoic acid phenyl ester (3l)[12] White
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solid; H NMR (400 MHz, CDCl3) δ: 8.07-8.04 (m,
2H), 7.48-7.40 (m, 4H), 7.32-7.23 (m, 3H), 2.47 (s,
3H); 13C NMR (100MHz, CDCl3) δ: 165.2, 150.8, 138.2,
134.2, 130.5, 129.3, 128.3, 127.2, 125.7, 121.6, 21.1.
3-Fluorobenzoic acid phenyl ester (3m)[16] White
4-Chlorobenzoic acid phenyl ester (3v)[11] White
solid; 1H NMR (400 MHz, CDCl3) δ: 8.14 (d, J=8.6 Hz,
2H), 7.48 (d, J=8.5 Hz, 2H), 7.43 (t, J=7.8 Hz, 2H),
7.28 (t, J=7.4 Hz, 1H), 7.20 (d, J=7.6 Hz, 2H); 13C
NMR (100 MHz, CDCl3) δ: 164.4, 150.8, 140.1, 131.6,
129.6, 128.6, 128.0, 126.1, 121.6.
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solid; H NMR (400 MHz, CDCl3) δ: 7.99-8.02 (m,
1H), 7.87-7.91 (m, 1H), 7.42-7.52 (m, 3H), 7.27-
7.37 (m, 2H) , 7.21-7.26 (m, 2H); 13C NMR (100 MHz,
CDCl3) δ: 163.7, 150.5, 131.5 (d, JCF=7.4 Hz), 130.1 (d,
JCF=7.7 Hz), 129.4, 125.9, 125.7 (d, JCF=2.9), 121.4,
120.6, 120.4, 116.9, 116.7.
2-Methylbenzoic acid phenyl ester (3w)[7a] Col-
3-Methoxybenzoic acid phenyl ester (3n)[13]
Colorless solid; 1H NMR (400 MHz, CDCl3) δ: 7.81 (d,
J=7.6 Hz, 1H), 7.71 (s, 1H), 7.42 (dd, J=15.1, 7.4 Hz,
3H), 7.29-7.16 (m, 4H), 3.87 (s, 3H); 13C NMR (100
MHz, CDCl3) δ: 165.1, 159.7, 150.9, 130.8, 129.6,
129.5, 125.9, 122.6, 121.7, 120.2, 114.6, 55.5.
orless oil; H NMR (400 MHz, CDCl3) δ: 8.20 (d, J=
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7.9 Hz, 1H), 7.53-7.45 (m, 3H), 7.38-7.23 (m, 5H),
2.71 (s, 3H); 13C NMR (100 MHz, CDCl3) δ: 165.9,
150.9, 141.4, 132.8, 132.0, 131.2, 129.5, 128.6, 126.0,
125.9, 121.9, 22.0.
4-Methylphenyl benzoate (3ab)[12] White solid;
1H NMR (400 MHz, CDCl3) δ: 8.23 (d, J=7.3 Hz, 2H),
7.63-7.68 (m, 1H), 7.53 (t, J=7.8 Hz, 2H), 7.25 (d,
J=8.1 Hz, 2H), 7.12-7.15 (m, 2H), 2.41 (s, 3H); 13C
NMR (100 MHz, CDCl3) δ: 164.4, 147.7, 134.5, 132.5,
129.2, 129.0, 128.7, 127.5, 120.4, 19.9.
2-Methylbenzoic acid phenyl ester (3o)[7a] Col-
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orless oil; H NMR (400 MHz, CDCl3) δ: 8.21 (d, J=
7.8 Hz, 1H), 7.45-7.57 (m, 3H), 7.24-7.39 (m, 5H),
2.72 (s, 3H); 13C NMR (100 MHz, CDCl3) δ: 165.8,
150.9, 141.3, 132.7, 131.9, 131.1, 130.1, 128.5, 125.9,
125.8, 121.8, 21.9.
4-Methoxyphenyl benzoate (3ac)[12] White solid;
1H NMR (400 MHz, CDCl3) δ: 8.21-8.24 (m, 2H),
7.62-7.67 (m, 1H), 7.53 (t, J=7.9 Hz, 2H), 7.14-
7.19 (m, 2H), 6.94-6.99 (m, 2H), 3.84 (s, 3H); 13C
NMR (100 MHz, CDCl3) δ: 164.5, 156.3, 143.4, 132.5,
129.1, 128.6, 127.6, 121.5, 113.5, 54.6.
2-Methoxybenzoic acid phenyl ester (3p)[7a]
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White crystal; H NMR (400 MHz, CDCl3) δ: 7.81 (d,
J=7.6 Hz, 1H), 7.68-7.70 (m, 1H), 7.40 (dd, J=15.2,
7.3 Hz, 3H), 7.14-7.28 (m, 4H), 3.86 (s, 3H); 13C
NMR (100 MHz, CDCl3) δ: 165.1, 159.7, 150.9, 130.8,
129.6, 129.5, 125.9, 122.6, 121.7, 120.2, 114.6, 55.5.
2-Thiophenecarboxylic acid phenyl ester (3q)[7a]
4-Chlorophenyl benzoate (3ad)[12] White solid;
1H NMR (400 MHz, CDCl3) δ: 8.18 (d, J=7.3 Hz, 2H),
7.63 (t, J=7.4 Hz, 1H), 7.50 (t, J=7.8 Hz, 2H), 7.38 (d,
J=8.7 Hz, 2H), 7.15 (d, J=8.7 Hz, 2H); 13C NMR (100
MHz, CDCl3) δ: 164.8, 149.3, 133.7, 131.2, 130.1,
129.4, 129.1, 128.5, 123.0.
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White crystal; H NMR (400 MHz, CDCl3) δ: 7.97-
7.99 (m, 1H), 7.64-7.66 (m, 1H), 7.39-7.43 (m, 2H),
7.24-7.28 (m 1H), 7.21 (d, J=8.0 Hz, 2H), 7.15-7.18
(m, 1H); 13C NMR (100 MHz, CDCl3) δ: 160.4, 150.3,
134.5, 133.3, 132.7, 129.3, 127.8, 125.8, 121.5.
Nicotinic acid phenyl ester (3r)[17] White crystal;
1H NMR (400 MHz, CDCl3) δ: 9.41 (d, J=1.8 Hz, 1H),
8.86 (dd, J=5.6, 1.5 Hz, 1H), 8.46 (dt, J=8.0, 1.9 Hz,
1H), 7.42-7.50 (m, 3H), 7.26-7.32 (m, 1H), 7.22-
7.25 (m, 2H); 13CNMR (100 MHz, CDCl3) δ: 162.9,
152.9, 150.3, 149.5, 136.7, 128.6, 125.3, 124.6, 122.5,
120.5.
4-tert-Butylphenyl benzoate (3ae)[18] Yellowish
solid; 1H NMR (400 MHz, CDCl3) δ: 8.20 (d, J=7.6 Hz,
2H), 7.62 (t, J=7.4 Hz , 1H), 7.47-7.52 (m, 2H), 7.43
(d, J=8.6 Hz, 2H), 7.14 (d, J=8.5 Hz, 2H), 1.34 (s,
9H); 13C NMR (100 MHz, CDCl3) δ: 165.2, 148.6,
148.5, 133.4, 130.1, 129.6, 128.4, 126.3, 120.9, 34.4,
31.3.
3-Methylphenyl benzoate (3af)[12] Colorless oil;
1H NMR (400 MHz, CDCl3) δ: 8.20 (d, J=6.6 Hz, 2H),
7.61 (t, J=7.6 Hz, 1H), 7.49 (t, J=7.8 Hz, 2H), 7.30 (t,
J=7.8 Hz, 1H), 7.07 (d, J=7.8 Hz, 1H), 7.03-7.00 (m,
2H), 2.38 (s, 3H); 13C NMR (100 MHz, CDCl3) δ: 165.2,
150.7, 139.5, 133.4, 130.0, 129.5, 129.0, 128.4, 126.5,
122.1, 118.5, 21.2.
Phenyl benzoate (3s)[11] White crystal; H NMR
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(400 MHz, CDCl3) δ: 8.19-8.22 (m, 2H), 7.61-7.66
(m, 1H), 7.49-7.53 (m, 2H), 7.41-7.46 (m, 2H),
7.20-7.29 (m, 3H); 13C NMR (100 MHz, CDCl3) δ:
165.2, 151.0, 133.6, 130.2, 129.6, 129.5, 128.6, 125.9,
121.7.
4-Methylbenzoic acid phenyl ester (3t)[11] White
3-Methoxyphenyl benzoate (3ag)[19] Colorless oil;
1H NMR (400 MHz, CDCl3) δ: 8.20 (d, J=7.5 Hz, 2H),
7.62 (t, J=7.5 Hz, 1H), 7.50 (t, J=7.8 Hz, 2H), 7.32 (t,
J=8.1 Hz, 1H), 6.84-6.77 (m, 3H), 3.80 (s, 3H); 13C
NMR (100 MHz, CDCl3) δ: 165.0, 160.5, 151.8, 133.5,
130.1, 129.8, 129.4, 128.5, 113.8, 111.8, 107.6, 55.3.
2-Methylphenyl benzoate (3ah)[12] Colorless oil;
1H NMR (400 MHz, CDCl3) δ: 8.27 (d, J=7.4 Hz, 2H),
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crystal; H NMR (400 MHz, CDCl3) δ: 8.09 (d, J=8.2
Hz, 2H), 7.42 (t, J=7.9 Hz, 2H), 7.29 (d, J=8.0 Hz,
2H), 7.24 (t, J=6.5 Hz, 1H), 7.21 (d, J=7.9 Hz, 2H),
2.45 (s, 3H); 13C NMR (100 MHz, CDCl3) δ: 165.2,
150.9, 144.3, 130.1, 129.4, 129.2, 126.8, 125.7, 121.7,
21.7.
4-Methoxybenzoic acid phenyl ester (3u)[12]
Chin. J. Chem. 2013, 31, 1488—1494
© 2013 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
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