7902
L. Zhou et al. / Tetrahedron Letters 48 (2007) 7899–7902
dioxane, toluene or THF. See: (a) Ref. 5; (b) Refs. 6a,b; (c)
References and notes
Ueda, M.; Saitoh, A.; Oh-tani, S.; Miyaura, N. Tetrahe-
dron 1998, 54, 13079–13086; (d) Percec, V.; Bae, J.-Y.;
Hill, D. H. J. Org. Chem. 1995, 60, 1060–1065.
1. (a) de Meijere, A.; Diederich, F. Metal-Catalyzed Cross-
Coupling Reactions, 2nd ed.; John Wiley & Sons: Wein-
heim, Germany, 2004; (b) Miyaura, N. Organoboron
Compouds. In Topics in Current Chemistry, Cross-Cou-
pling Reactions; Miyaura, N., Ed.; Springer, 2002; Vol.
219, pp 11–59; For a review, see: (c) Bellina, F.; Carpita,
A.; Rossi, R. Synthesis 2004, 15, 2419–2440.
2. Aryl triflates were used as Suzuki coupling partners, see:
Kabalka, G. W.; Zhou, L.-L.; Naravane, A. Tetrahedron
Lett. 2006, 47, 6887–6889.
3. Aryl sulfonates were used as Suzuki coupling partners, see:
Lakshman, M. K.; Gunda, P.; Pradhan, P. J. Org. Chem.
2005, 70, 10329–10335.
4. Recently, Nolan, S. P. et al. reported that N-heterocyclic
carbenes (NHC) can be used as effective ligands for Pd-
catalyzed Suzuki coupling of aryl chlorides with aryl-
boronic acids. See: Navarro, O.; Kelly, R. A.; Nolan, S. P.
J. Am. Chem. Soc. 2003, 125, 16194–16195.
15. Recently, N-heterocyclic carbenes have attracted consid-
erable attention as an efficient ligand for Pd or Ni-
catalyzed Suzuki coupling. See: (a) Ref. 4. (b) Ref. 61.
16. The complex [NiCl(Ph2PCH2CH2OH)2(H2O)]Cl (5) was
prepared by the following procedure: A solution of
NiCl2Æ6H2O (0.48 g, 2.0 mmol) dissolved in minimum
amounts of ethanol was added to
a solution of
Ph2PCH2CH2OH (1.01 g, 4.4 mmol) in 50 mL of ether,
and after the reaction mixture with grape color was stirred
for 16 h, a lot of green solid formed. The resulting mixture
was filtered to produce green solid. Recrystallization of the
crude product from ethanol/ether afforded 5 as green
crystals (0.73 g, 60% yield). MS (API-ES): m/z: 517.1
[M–H2O–2Cl–H]+; Anal. Calcd for C28H32Cl2NiO3P2: C,
55.30; H, 5.30. Found: C, 55.72; H, 5.50. X-ray crystallo-
graphic analysis was carried out on a Rigaku AFC7R
diffractometer using a rotating anode with graphite
5. Saito, S.; Sakai, M.; Miyaura, N. Tetrahedron Lett. 1996,
37, 2993–2996.
˚
monochromated Mo Ka radiation (k = 0.71073 A). Crys-
tal data for 5: C28H32Cl2NiO3P2, M = 608.10, space group:
6. (a) Saito, S.; Oh-tani, S.; Miyaura, N. J. Org. Chem. 1997,
62, 8024–8030; (b) Indolese, A. F. Tetrahedron Lett. 1997,
38, 3513–3516; (c) Galland, J.-C.; Savignac, M.; Geneˆt,
J.-P. Tetrahedron Lett. 1999, 40, 2323–2326; (d) Lead-
beater, N. E.; Resouly, S. M. Tetrahedron 1999, 55, 11889–
11894; (e) Inada, K.; Miyaura, N. Tetrahedron 2000, 56,
8657–8660; (f) Lipshutz, B. H.; Sclafani, J. A.; Blomgren,
P. A. Tetrahedron 2000, 56, 2139–2144; (g) Percec, V.;
Golding, G. M.; Smidrkal, J.; Weichold, O. J. Org. Chem.
2004, 69, 3447–3452; (h) Tang, Z.-Y.; Hu, Q.-S. J. Am.
Chem. Soc. 2004, 126, 3058–3059; (i) Zhou, J.-R.; Fu,
G. C. J. Am. Chem. Soc. 2004, 126, 1340–1341; (j) Tang,
Z.-Y.; Spinella, S.; Hu, Q.-S. Tetrahedron Lett. 2006, 47,
2427–2430; (k) Tang, Z.-Y.; Hu, Q.-S. J. Org. Chem. 2006,
71, 2167–2169; (l) Lee, C.-C.; Ke, W.-C.; Chan, K.-T.; Lai,
C.-L.; Hu, C.-H.; Lee, H. M. Chem. Eur. J. 2007, 13, 582–
591; (m) Chen, C.; Yang, L.-M. Tetrahedron Lett. 2007,
48, 2427–2430.
˚
˚
monoclinic, C2/c, a = 17.8864(11) A, b = 8.5177(6) A,
˚
c = 38.512(3) A, a = 90.00(0)°, b = 102.164(3)°, c =
3
˚
90.00(0)°, V = 5735.7(7) A, T = 273(2) K, Z = 8, Dc =
1.399 g cmꢀ3, l = 1.002 mmꢀ1, goodness of fit = 1.020, R1
[I > 2r(I)] = 0.0499, wR2 = 0.1260. Selected bond dis-
˚
tances (A) and angles (°) are shown as follows: Ni(1)–
O(1) 2.109(5), Ni(1)–O(2) 2.149(5), Ni(1) –O(3) 2.125(5),
Ni(1)–Cl(1) 2.331(2), Ni(1)–P(1) 2.360(2), Ni(1)–P(2)
2.469(2), O(1)–Ni(1)–O(3) 82.0(2), O(1)–Ni(1)–O(2)
86.7(2), O(3)–Ni(1)–O(2) 84.0(2), O(1)–Ni(1)–Cl(1)
91.15(15), O(3)–Ni(1)–Cl(1) 91.67(16), O(2)–Ni(1)–Cl(1)
175.36(14), O(1)–Ni(1)–P(1) 168.35(15), O(3)–Ni(1)–P(1)
93.86(16), O(2)–Ni(1)–P(1) 82.01(15), Cl(1)–Ni(1)–P(1)
99.89(8), O(1)–Ni(1)–P(2) 80.31(15), O(3)–Ni(1)–P(2)
158.57(17), O(2)–Ni(1)–P(2) 83.01(13), Cl(1)–Ni(1)–P(2)
100.71(8), P(1)–Ni(1)–P(2) 101.07(8). Atomic coordinates,
other bond lengths, and other angles and the other
important parameters have been deposited with the Cam-
bridge Crystallographic Data Centre as supplementary
publication, CCDC No. 626494. Copies of this informa-
tion can be obtained, free of charge, on application to
CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax:
+44-1233-336033 or e-mail: deposit@ccdc.cam.ac.uk).
17. Siclair, D. J.; Sherburn, M. S. J. Org. Chem. 2005, 70,
3730–3733.
18. General procedure for the coupling of aryl chlorides with
arylboronic acids: A mixture of aryl chloride (0.5 mmol),
arylboronic acid (0.75 mmol), potassium phosphate
(1.0 mmol), complex 5 in 2 mL of IPA was stirred at
80 °C under a nitrogen atmosphere for 4–24 h. The
reaction progress was monitored by TLC, and aryl
chloride disappeared after 2–24 h. When the reaction
completed, the mixture was cooled to room temperature,
then was filtered by a short silica gel column to afford a
crude product. Further purification of the product was
performed by a chromatography on silica gel column
[petroleum ether (60–90 °C)/ethyl acetate = 100:0 to 20:1].
19. Son, S. U.; Kim, S. B.; Reingold, J. A.; Carpenter, G. B.;
Sweigart, D. A. J. Am. Chem. Soc. 2005, 127, 12238–
12239.
´
7. Gonzalez-Bobes, F.; Fu, G. C. J. Am. Chem. Soc. 2006,
128, 5360–5361.
8. (a) See Ref. 7; (b) See Ref. 4.
9. Guo, M.-P.; Jian, F.-F.; He, R. Tetrahedron Lett. 2005,
46, 9017–9020.
10. PPh3 was an effective ligand for Ni-catalyzed cross-
coupling of aryl chlorides with arylboronic acids in
dioxane, toluene or THF. See: (a) Ref. 6e; (b) Ref. 6k.
11. PCy3 has been utilized as a effective ligand for Ni-
catalyzed coupling of aryl tosylates and aryl chlorides with
arylboronic acids in THF or dioxane. See: (a) Ref. 6h; (b)
Zim, D.; Lando, V. R.; Dupont, J.; Monterio, A. L. Org.
Lett. 2001, 3, 3049–3051.
12. NEt3and 2,20-bipyridine have been used as ligands instead
of phosphines, for Ni-catalyzed coupling of aryl halides
with arylboronic acids in dioxane. See: Ref. 6d.
13. DPPE can be used as a ligand for Ni-catalyzed coupling of
aryl chlorides, aryl mesylates or aryl sulfonates with
arylboronic acids in dioxane/H2O or dioxane. See: (a) Ref.
6c; (b) Ref. 6g.
14. A numbers of papers have demonstrated that DPPF is
more effective ligand for Ni-catalyzed coupling of aryl
chlorides or aryl mesylates with arylboronic acids in