Palladium-Catalyzed Suzuki Reaction Using 1,3-Dialkylbenzimidazol-2-ylidene Ligands in Aqueous Media 423
Krafczyk, R.; Schmutzler, R.; Craig, H. A.; Goerlich,
J. R.; Marshall, W. J.; Unverzagt, M. Tetrahedron
1999, 55, 14523–14534.
1-buthyl chloride (0.64 g, 6.87 mmol) in DMF
(1 mL). Yield: 1,84 g, 84%, mp 156–157◦C. IR,
ꢁ: 1565 cm−1 (C N). 1H NMR (CDCl3) δ: 0.90
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G. Chem Rev 2000, 100, 39–92; (b) Weskamp, T.;
Bo¨hm, V. P. W.; Herrmann, W. A. J Organomet Chem
2000, 600, 12–22.
(t, J = 7.2 Hz, 3H, CH2CH2CH2CH ), 1.32 (m, 2H,
3
CH2CH2CH CH3), 1.38 (m, 6H, CH2(CH )3CH2), 1.89
2
2
(p, J = 7.2 Hz, 2H, CH2CH CH2CH3), 2.38 (m, 4H,
2
[7] Herrmann, W. A. In Applied Homogeneous Cataly-
sis with Organometallic Compounds; eds. Cornils, B.;
Herrmann, W. A.; (Eds.); VCH: Weinhem, 1996.
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213; (b) Herrmann, W. A.; Ko¨cher, C. Angew Chem
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Angew Chem Int Ed Eng 2002, 41, 1290–1309.
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Synth Catal 2002, 344, 585–595; (b) Bielowski, C. W.;
Grubbs, R. H. Angew Chem Int Ed Eng 2000, 39,
2903–2906; (c) Herrmann, W. A.; Reisinger, C. P.;
Spiegler, M. J Organomet Chem 1998, 557, 93–96;
(d) Weskamp, T.; Bo¨hm, V. P. W.; Herrmann, W. A.
J Organomet Chem 1999, 585, 348–352.
CH (CH2)3CH ), 2.74 (m, 2H, NCH2CH N), 4.55
2
2
2
(t, J =7.2 Hz, 2H, CH CH2CH2CH3), 4.64 (m, 2H,
2
NCH CH2N), 7.64–8.13 (m, 4H, Ar-H), 10.07 (s, 1H,
2
2-CH). 13C NMR (CDCl3) δ: 14.4, 20.1, 31.7, 54.8
(CH2(CH2)2CH3), 24.6, 26.6, 45.4 (CH2(CH2)3CH2),
47.4, 56.2 (NCH2CH2N), 114.8, 114.9, 127.5, 132.0,
132.2 (Ar-C), 143.9 (2-CH). Found: C, 67.56; H, 8.12;
N, 13.21%. Calcd for C18H28N3Cl: C, 67.16; H, 8.76;
N, 13.05%.
General Procedure for the Suzuki-Type
Coupling Reactions
¨
˙
¨
[10] (a) Ozdemir, I.; Yigˇit, B.; C¸ etinkaya, B.; Ulku¨, D.; Tahir,
M. N.; Arıcı, C. J Organomet Chem 2001, 633, 27–32;
¨
˙
Pd(OAc)2 (1.5 mmol %), 1,3-dialkylbenzimidazolium
salt, 2a–c and 4a–c (3 mmol %), aryl chloride
(1.0 mmol), phenylboronic acid (1.5 mmol), Cs2CO3
(2 mmol), and water (3 mL)–DMF (3 mL) were added
in a small Schlenk tube under argon and the mix-
ture was heated at 80◦C for 6 h. At the conclusion
of the reaction, the mixture was cooled, extracted
with Et2O, filtered through a pad of silicagel with co-
pious washings, concentrated, and purified by flash
chromatography on silicagel. Purity of compounds
was checked by NMR and the yields are based on
arylchloride.
(b) C¸ etinkaya, B.; Gu¨rbu¨z, N.; Ozdemir, I.; Sec¸kin, T.
J Mol Catal A 2002, 184, 31–38.
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2000, 19, 741–748.
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37, 3387–3388.
[13] Herrmann, W. A.; Bo¨hm, V. P. W. J Organomet Chem
1999, 576, 23–41.
[14] Li, C. J.; Chan, T. H. Organic Reactions in Aqueous
Media; Wiley: New York, 1997.
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Hirao, T. J Org Chem 2002, 67, 2721–2722; (c) Parisot,
S.; Kolodziuk, R.; Henry, C. G.; Iourtchenko, A.;
Sinou, D. Tetrahedron Lett 2002, 43, 7397–7400.
[16] Botella, L.; Najera, C. Angew Chem Int Ed Eng 2002,
41, 179–181.
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