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16. Synthesis of Potassium Oxalate monoesters. According to the literature
7
.
.
procedure,
a 100 mL flask was charged with diethyl oxalate (13.5 mL,
4
6, 9049.
(a) Shang, R.; Fu, Y.; Li, J. B.; Zhang, S. L.; Guo, Q. X.; Liu, L. J. Am. Chem. Soc. 2009,
31, 5738; (b) Shang, R.; Fu, Y.; Wang, Y.; Xu, Q.; Yu, H. Z.; Liu, L. Angew. Chem.,
0.1 mol), potassium acetate (9.8 g, 0.1 mol), and ethanol (20 mL) as solvents.
Subsequently water (1.8 mL, 0.1 mol) was added via syringe. The mixture was
stirred under reflux condition (90 °C oil bath) for 3 h, and a lot of white crystal
solid was obtained. The mixture was allowed to cool to room temperature and
20 mL diethyl ether was added. The white crystal was filtrated, washed with
ethanol and diethyl ether, and dried under vacuum at 30 °C for 2 h.
8
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Int. Ed. 2009, 48, 9350; (c) Shang, R.; Xu, Q.; Jiang, Y. Y.; Wang, Y.; Liu, L. Org.
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17. General experimental procedure. An oven-dried Schlenk-tube (10 mL) was
charged with Pd source (1 mol %), and ethyl potassium oxalate (0.75 mmol).
The tube was evacuated and backfilled with argon (this procedure was
repeated three times). After that, iodobenzene (0.5 mmol) and NMP (1.0 mL)
were added by syringe under a counter flow of argon at room temperature. The
reaction vessel was closed and then placed under stirring in a preheated oil
bath. The reaction mixture was stirred for 24 h. Upon completion of the
reaction, the mixture was cooled to room temperature and diluted with ethyl
acetate, and analyzed by gas chromatography. Selected spectral and analytical
9
.
15, 3674; (d) Miyasaka, M.; Hirano, K.; Satoh, T.; Miura, M. Adv. Synth. Catal.
2
2
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data for 4-methylbenzoic acid ethyl ester (3a): 1H NMR (400 MHz, CDCl
(t, 3H, J = 7.2 Hz), 2.39 (s, 3H), 4.36 (q, 2H, J = 7.1 Hz), 7.22 (d, 2H, J = 8.4 Hz),
7.93 (d, 2H, J = 8.4 Hz). 13C NMR (100 MHz, CDCl
, d ppm): 14.4, 21.7, 60.8,
127.8, 129.1, 129.6, 143.4, 166.7. HRMS calcd C10 : 164.0837. Found:
164.0826. 4-Chlorobenzoic acid ethyl ester (3g): 1H NMR (400 MHz, CDCl
): d
1.39 (t, 3H, J = 7.0 Hz), 4.36 (q, 2H, J = 7.1 Hz), 7.38–7.42 (m, 2H), 7.96–7.99 (m,
2H). 13C NMR (100 MHz, CDCl
, d ppm): 14.4, 61.3, 128.8, 129.0, 131.0, 139.3,
165.8. HRMS calcd C ClO : 184.0291. Found: 184.0282. 4-Nitrobenzoic acid
ethyl ester (3m): 1H NMR (400 MHz, CDCl
): d 1.44 (t, 3H, J = 7.0 Hz), 4.43 (q,
2H, J = 7.2), 8.20–8.23 (m, 2H), 8.27–8.30 (m, 2H). C NMR (100 MHz, CDCl
3
): d 1.37
12, 592; (g) Yamashita, M.; Hirano, K.; Satoh, T.; Miura, M. Adv. Synth. Catal.
2
011, 353, 631.
3
1
0. (a) Cornella, J.; Lu, P.; Larrosa, I. Org. Lett. 2009, 11, 5506; (b) Grainger, R.;
Nikmal, A.; Cornella, J.; Larrosa, I. Org. Biomol. Chem. 2012, 10, 3172; (c)
Cornella, J.; Lahlali, H.; Larrosa, I. Chem. Commun. 2010, 46, 8276; (d) Cornella,
J.; Larrosa, I. Synthesis 2012, 653.
12 2
H O
3
3
1
1. (a) Zhang, M.; Zhou, J.; Kan, J.; Wang, M.; Su, W. P.; Hong, M. C. Chem. Commun.
9
H
9
2
2
010, 46, 5455; (b) Zhao, H. Q.; Wei, Y.; Xu, J.; Kan, J.; Su, W. P.; Hong, M. C. J.
3
13
Org. Chem. 2011, 76, 882; (c) Zhou, J.; Hu, P.; Zhang, M.; Huang, S. J.; Wang, M.;
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Org. Lett. 2010, 12, 4992; (e) Hu, P.; Kan, J.; Su, W. P.; Hong, M. Org. Lett. 2009,
3
, d
NO
ppm): 14.3, 62.0, 123.4, 130.7, 135.9, 150.5, 164.7. HRMS calcd C
195.0532. Found: 195.0545.
H
9 9
4
:
11, 2341; (f) Hu, P.; Shang, Y. P.; Su, W. P. Angew. Chem., Int. Ed. 2012, 51, 5945.
18. Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 14844.
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Wang, Z. Y.; Ding, Q. P.; He, X. D.; Wu, J. Tetrahedron 2009, 65, 4635; (c) Luo, Y.;