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10. Typical experimental procedure: To a round bottomed
flask containing CuI (0.5 mol %) and benzotriazole
(1.0 mol %) in 1 ml of DMSO, 1 mmol of aryl halide was
added and the reaction stirred for 10 min. Next, 1 mmol of
arylthiol (or alkylthiol) and 1.4 equiv of KOt-Bu were
added and the reaction mixture was stirred vigorously for
10–18 h at 100 ꢁC (80 ꢁC for thiols). After completion of
the reaction (monitored by TLC), ethyl acetate 10 mL was
added and the reaction mixture was washed with water
(3 · 10 mL) and combined organics dried over Na2SO4
and evaporated under vacuum. The residue was purified
by column chromatography (hexanes) to afford the
corresponding desired product. All the products
have been characterized by 1H NMR, 13C NMR and
mass spectroscopy. Table 2, entry 4 (3d): colourless
oil, 1H NMR (300 MHz, CDCl3): d = 7.58–7.51 (m,
3H), 7.48–7.35 (m, 8H), 7.33–7.21 (m, 3H); 13C NMR
(100 MHz, CDCl3): d = 140.3, 140.2, 139.9, 134.4, 131.2,
131.1, 129.6, 128.8, 127.8, 127.5, 127.1, 127.0; TOF-MS
ES m/z: 261.069 (MÀ1). Table 2, entry 5 (3e): colourless
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5. For a review, see: (a) Muci, A. R.; Buchwald, S. L.
Practical Palladium Catalysts for C–N and C–O Bond
Formation. In Topics in Current Chemistry; Miyaura, N.,
Ed.; Springer: Berlin, 2002; Vol. 219, p 133.
6. (a) Kondo, T.; Mitsudo, T. Chem. Rev. 2000, 100, 3205;
Using stoichiometric Cu2O reagent in a 1:4 pyridine–
quinoline solvent at 160 ꢁC (b) Pinchart, A.; Dallaire, C.;
Gingras, M. Tetrahedron Lett. 1998, 39, 543; Using
1
oil, H NMR (300 MHz, CDCl3): d = 8.42–8.39 (m, 1H),
7.51–7.39 (m, 3H), 7.26 (d, 1H, J = 2.7 Hz), 7.23 (s, 1H),
6.99–6.95 (m, 1H), 6.33 (dt, 1H, J = 0.9, 6.3 Hz), 2.39 (s,
3H); 13C NMR (100 MHz, CDCl3): d = 162.2, 149.5,
139.4, 136.6, 135.2, 130.4, 127.2, 120.8, 119.6, 21.3; TOF-
MS ES m/z: 202.211 (M+1). Table 2, entry 6 (3f): yellow
crystals, mp = 68–70 ꢁC 1H NMR (300 MHz, CDCl3):
d = 9.89 (s, 1H), 7.71–7.67 (m, 2H), 7.45–7.42 (m, 2H),
7.25 (d, 2H, J = 8.4 Hz), 7.18 (dd, 2H, J = 1.8, 5.1 Hz),
2.41 (s, 3H); 13C NMR (100 MHz, CDCl3): d = 191.1,
148.1, 139.7, 134.8, 133.4, 130.6, 130.0, 127.2, 126.5, 21.3;
TOF-MS ES m/z: 227.132 (MÀ1).
´
5 mol % of Cu in refluxing NMP: (c) Sindelar, K.;
´
´
´
´
Hrubantova, M.; Svatek, E.; Matousova, O.; Metysova,
´
J.; Valchar, M.; Protiva, M. Collect. Czech. Chem.
Commun. 1989, 54, 2240; Use of a stoichiometric amount
of CuI to prepare S-arylated cysteine derivatives at 100 ꢁC