Paper
NJC
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(m, 18H), 0.78 (d, J = 6.8 Hz, 3H); 13C-NMR (62.9 MHz, CDCl3)
Phenethyl-4-cyanobenzoate (6ia0). H-NMR (250 MHz, CDCl3)
d (ppm): 192.0, 137.2, 133.1, 128.5, 127.1, 31.9, 29.6, 29.6, 29.5, d (ppm): 8.01 (d, J = 7.5 Hz, 2H), 7.63 (d, J = 7.5 Hz, 2H), 7.22–
29.5, 29.3, 29.1, 29.0, 29.0, 28.9, 22.7, 14.1.
7.17 (m, 5H), 4.49 (t, J = 6.9 Hz, 2H), 3.01 (t, J = 6.9 Hz, 2H);
13C-NMR (62.9 MHz, CDCl3) d (ppm): 164.7, 137.5, 134.0, 132.2,
130.0, 128.8, 128.6, 126.7, 117.9, 116.3, 66.1, 35.0; anal. calcd
for C16H13NO2: C, 76.48; H, 5.21; N, 5.57. Found: C, 76.38;
H, 5.12; N, 5.70.
S-(sec-Butyl)benzothioate (3af0). 1H-NMR (250 MHz, CDCl3)
d (ppm): 7.90–7.76 (m, 2H), 7.47–7.43 (m, 1H), 7.38–7.34
(m, 2H), 3.72–3.59 (m, 1H), 1.93–1.45 (quint, J = 7.5 Hz, 2H),
1.31 (d, J = 6.9 Hz, 3H), 0.93 (t, J = 7.4 Hz, 3H); 13C-NMR
(62.9 MHz, CDCl3) d (ppm): 192.1, 137.4, 133.1, 128.5, 127.1,
41.1, 29.6, 20.9, 11.5.
Methyl phenethyl terephthalate (6ja0). 1H-NMR (250 MHz,
CDCl3) d (ppm): 7.80–7.76 (m, 4H), 7.07–7.96 (m, 5H), 4.28
(t, J = 7.5 Hz, 2H), 3.65 (s, 3H), 2.81 (t, J = 7.5 Hz, 2H); 13C-NMR
S-Pentyl-4-methylbenzothioate (3bd0). 1H-NMR (250 MHz, (62.9 MHz, CDCl3) d (ppm): 166.1, 165.5, 137.6, 134.0, 133.8,
CDCl3) d (ppm): 7.78 (d, J = 8.2 Hz, 2H), 7.15 (d, J = 8.2 Hz, 129.4, 129.3, 128.9, 128.54, 126.6, 65.8, 52.3, 35.1.
2H), 2.97 (t, J = 7.3 Hz, 2H), 2.31 (m, 3H), 1.62–1.15 (m, 2H),
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Benzyl benzoate (6ad0). H-NMR (250 MHz, CDCl3) d (ppm):
1.36–1.23 (m, 4H), 0.83 (t, J = 6.9 Hz, 3H); 13C-NMR (62.9 MHz,
7.98 (dd, J = 8.1, 1.1 Hz, 2H), 7.44–7.35 (m, 1H), 7.34–7.23
CDCl3) d (ppm): 191.7, 143.9, 134.7, 129.1, 127.2, 31.0, 29.2,
(m, 7H), 5.26 (s, 2H); 13C-NMR (62.9 MHz, CDCl3) d (ppm):
28.6, 22.2, 21.6, 13.9.
166.4, 136.0, 133.0, 130.1, 129.7, 128.6, 128.4, 128.2, 128.1, 66.7.
Naphthalen-1-yl benzoate (6af0). 1H-NMR (250 MHz, CDCl3)
d (ppm): 8.26–8.22 (m, 2H), 7.86–8.77 (m, 2H), 7.68 (d, J =
General procedure for the Ni-catalyzed alkoxycarbonylation of
aryl iodides
Alcohol (2.5 mmol) was added to a mixture of Cr(CO)6 (1.0 mmol, 8.2 Hz, 1H), 7.57–7.54 (m, 1H), 7.48–7.37 (m, 5H), 7.28 (dd, J =
0.22 g), iodoarene (1.0 mmol), NiCl2 (16.0 mol%, 0.02 g), and 7.5, 0.9 Hz, 1H); 13C-NMR (62.9 MHz, CDCl3) d (ppm); 165.2,
Et3N (3.0 mmol, 0.42 mL) in DMF (3.0 mL) in a round-bottom 146.8, 134.7, 133.8, 130.3, 129.4, 128.7, 128.1, 127.0, 126.5,
flask. The reaction mixture was stirred for the appropriate time at 126.5, 126.1, 125.5, 121.2, 118.2.
100 1C, and then H2O (10.0 mL) was added to the cooled reaction
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Naphthalen-2-yl benzoate (6ag0). H-NMR (250 MHz, CDCl3)
mixture. The extraction of the organic layer with EtOAc (3 ꢀ
d (ppm): 8.17–8.13 (m, 2H), 7.81–7.71 (m, 3H), 7.59–7.50
10 mL) was followed by drying (Na2SO4) and filtration. The
(m, 2H), 7.44–7.36 (m, 4H), 7.26 (m, 1H); 13C-NMR (62.9 MHz,
removal of the solvent provided a crude mixture, which was
CDCl3) d 165.4, 148.6, 133.8, 133.6, 131.5, 130.2, 129.5, 129.5,
purified by column chromatography with silica gel using n-hexane/
128.6, 127.8, 127.7, 126.6, 125.7, 121.3, 118.7.
EtOAc as the eluent to deliver the desired ester in high yield.
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p-Tolyl benzoate (6ah0). H-NMR (250 MHz, CDCl3) d (ppm):
Spectral data for the selected esters
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Phenethyl-2-methylbenzoate (6da0). H-NMR (250 MHz, CDCl3)
8.24 (d, J = 7.5 Hz, 2H), 7.66–7.62 (m, 1H), 7.55–7.49 (m, 2H),
7.25 (d, J = 7.5 Hz, 2H), 7.13 (d, J = 7.5 Hz, 2H), 2.40 (s, 3H); 13
C
d (ppm): 7.91 (d, J = 7.5 Hz, 1H), 7.44–7.27 (m, 8H), 4.56 (t, J =
7.2 Hz, 2H), 3.11 (t, J = 7.3 Hz, 2H), 2.59 (s, 3H); 13C-NMR
(62.9 MHz, CDCl3) d (ppm): 166.1, 145.5, 134.8, 132.4, 131.5,
131.4, 130.7, 129.8, 128.2, 127.3, 132.2, 67.1,36.1, 17.5.
NMR (62.9 MHz, CDCl3) d (ppm): 165.3, 148.7, 135.5, 133.5,
130.1, 130.0, 129.6, 128.5, 121.3, 20.9.
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2-Cyclohexylethyl benzoate (6aj0). H-NMR (250 MHz, CDCl3)
Phenethyl-3,4-dichlorobenzoate (6ea0). 1H-NMR (250 MHz,
CDCl3) d (ppm): 8.00 (d, J = 2.5 Hz, 1H), 7.74 (dd, J = 8.4,
2.0 Hz, 1H), 7.43 (d, J = 7.5 Hz, 1H), 7.27–7.15 (m, 5H), 4.45
(t, J = 7.0 Hz, 2H), 3.00 (t, J = 7.0 Hz, 2H); 13C-NMR (62.9 MHz,
CDCl3) d (ppm): 164.6, 137.5, 137.5, 132.9, 131.5, 130.5, 130.0,
128.9, 128.9, 128.6, 126.7, 65.8, 35.1; anal. calcd for
d (ppm): 8.05 (dd, J = 8.4, 1.4 Hz, 2H), 7.58–7.51 (m, 1H), 7.46–
7.40 (m, 2H), 4.36 (t, J = 6.8 Hz, 2H), 1.80–1.63 (m, 8H), 1.53–
1.39 (m, 2H), 1.28–1.20 (m, 1H), 1.04–0.91 (m, 2H); 13C-NMR
(62.9 MHz, CDCl3) d (ppm): 166.6, 132.7, 130.5, 129.5, 128.3,
63.2, 36.0, 34.7, 33.1, 26.4, 26.2.
m-Tolyl benzoate (6ak0). 1H NMR (250 MHz, CDCl3) d (ppm):
8.12 (dd, J = 6.9, 1.5 Hz, 2H), 7.53–7.51 (m, 1H), 7.48–7.44–7.38
(m, 2H), 7.22 (t, J = 7.5 Hz, 1H), 7.01–6.91 (m, 3H), 2.30 (s, 3H);
13C NMR (62.9 MHz, CDCl3) d (ppm): 165.2, 150.9, 139.6, 133.5,
130.1, 129.6, 129.2, 128.5, 126.7, 122.3, 118.6, 21.3.
C
15H12Cl2O2: C, 61.04; H, 4.10. Found: C, 61.18; H, 4.05.
Phenylethyl-4-(trifluoromethyl)benzoate (6fa0). 1H-NMR (250 MHz,
CDCl3) d (ppm): 8.12 (d, J = 7.5 Hz, 2H), 7.70 (d, J = 8.5 Hz, 2H),
7.34–7.26 (m, 5H), 4.58 (t, J = 7.5 Hz, 2H), 3.10 (t, J = 7.1 Hz, 2H);
13C-NMR (62.9 MHz, CDCl3) d (ppm): 165.2, 137.8, 132.7 (q, J =
31.5 Hz), 130.8, 129.9, 128.9, 128.6, 126.7, 125.3 (q, J = 3.7 Hz), 123.5
(q, J = 271.2 Hz), 65.8, 35.1.
2-Methyl-1-phenylpropan-2-yl benzoate (6al0). 1H-NMR (250 MHz,
CDCl3) d (ppm): 7.91–7.87 (m, 2H), 7.45–7.41 (m, 1H), 7.36–7.30
(m, 2H), 7.19–7.17 (m, 5H), 3.15 (s, 2H), 1.51 (t, J = 0.3 Hz, 6H);
13C-NMR (62.9 MHz, CDCl3) d (ppm): 164.0, 137.1, 132.4, 130.6,
129.7, 129.4, 128.1, 127.9, 126.4, 66.7, 46.6, 26.1.
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Diphenethyl-terephthalate (6ha0). H-NMR (250 MHz, CDCl3)
d (ppm): 8.08 (s, 4H), 7.35–7.25 (m, 10H), 4.57 (t, J = 7.2 Hz, 2H),
3.11 (t, J = 7.2 Hz, 2H); 13C-NMR (62.9 MHz, CDCl3) d (ppm):
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Octyl 4-methoxybenzoate (6cm0). H-NMR (250 MHz, CDCl3)
165.6, 137.7, 134.0, 129.5, 128.9, 128.6, 126.7, 65.8, 35.1; anal. d (ppm): 7.89 (d, J = 7.5 Hz, 2H), 6.80 (d, J = 7.5 Hz, 2H), 4.18
calcd for C24H22O4: C, 76.99; H, 5.92. Found: C, 76.90; H, 5.95. (t, J = 6.8 Hz, 2H), 3.74 (s, 3H), 1.70–1.59 (m, 2H), 1.32–1.18
New J. Chem.
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