R. Rama Suresh, K. C. Kumara Swamy / Tetrahedron Letters 50 (2009) 6004–6007
6007
6. (a) Correa, A.; Bolm, C. Angew. Chem., Int. Ed. 2007, 46, 8862; (b) Correa, A.;
Bolm, C. Chem. Eur. J. 2008, 14, 3527; (c) Correa, A.; Bolm, C. Adv. Synth. Catal.
2008, 350, 391.
Inorg. Chem. 2007, 46, 9819; (e) Bhuvan Kumar, N. N.; Kumara Swamy, K. C.
Tetrahedron Lett. 2008, 49, 7135.
13. X-ray data were collected on a Bruker AXS SMART diffractometer using Mo K
a
7. (a) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176; (b) Li, G. Y. Angew.
Chem., Int. Ed. 2001, 40, 1513; (c) Chen, G.; Lam, W. H.; Fok, W. S.; Lee, H. W.;
Kwong, F. Y. Chem. Asian J. 2007, 2, 306; (d) Shen, Q.; Ogata, T.; Hartwig, J. F. J.
Am. Chem. Soc. 2008, 130, 6586.
(k = 0.71073 Å) radiation. The structures were solved and refined by standard
methods. Crystal data for 4: C12H11NF6O, M = 299.22, monoclinic, space group
P2(1)/n, a = 9.338, b = 7.752, c = 17.542 Å, b = 98.38°, V = 1256.3(4) Å3, Z = 4,
l
= 0.161 mmÀ1, data/restraints/parameters: 2212/0/235, R indices (I > 2
r(I)):
8. (a) Zim, D.; Buchwald, S. L. Org. Lett. 2003, 5, 2413; (b) Strieter, E. R.; Blackmond,
D. G.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 13978; (c) Wolfe, J. P.;
Buchwald, S. L. Angew. Chem., Int. Ed. 1999, 38, 2413; (d) Huang, X.; Anderson, K.
W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125,
6653; (e) Li, G. Y.; Zheng, G.; Noonan, A. F. J. Org. Chem. 2001, 66, 8677; (f) Li, G. Y.
U.S. Patent 20040147392, 2004; Chem. Abstr. 2004, 141, 142192.
9. (a) Marion, N.; Navarro, O.; Mei, J.; Stevens, E. D.; Scott, N. M.; Nolan, S. P. J. Am.
Chem. Soc. 2006, 128, 4101; (b) Suzuki, K.; Hori, Y.; Kobayashi, T. Adv. Synth.
Catal. 2008, 350, 652.
R1 = 0.0843, wR2 (all data) = 0.2530. The trifluoromethyl groups showed some
disorder, but the molecule as such refined well. CCDC no. 739921.
14. Urgaonkar, S.; Verkade, J. G. J. Org. Chem. 2004, 69, 9135.
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3107.
16. Allcock, H. R. Inorg. Synth. 1972, 25, 8.
17. General procedure for the amination of aryl chlorides and bromides: All the
compounds reported here are well-known. In an oven-dried Schlenk tube, 1 mL
of Ligand
1 (R = Cl) (33 mg, 0.12 mmol, 12 mol %) of 0.120 M solution in
10. (a) Ackermann, L.; Spatz, J. H.; Gschrei, C. J.; Born, R.; Althammer, A. Angew.
Chem., Int. Ed. 2006, 45, 7627; (b) Ackermann, L.; Born, R. Angew. Chem., Int. Ed.
2005, 44, 2444.
11. (a) Balakrishna, M. S.; Mague, J. T. Organometallics 2007, 26, 4677; (b)
Chandrasekaran, P.; Mague, J. T.; Balakrishna, M. S. Polyhedron 2008, 27, 80.
12. (a) Satish Kumar, N.; Praveen Kumar, K.; Pavan Kumar, K. V. P.; Kommana, P.;
Vittal, J. J.; Kumara Swamy, K. C. J. Org. Chem. 2004, 69, 1880; (b) Kumara
Swamy, K. C.; Kumar, K. P.; Bhuvan Kumar, N. N. J. Org. Chem. 2006, 71, 1002;
(c) Bhuvan Kumar, N. N.; Chakravarty, M.; Kumara Swamy, K. C. New J. Chem.
2006, 30, 1614; (d) Chakravarty, M.; Rama Suresh, R.; Kumara Swamy, K. C.
toluene, Pd2dba3 (28 mg, 0.03 mmol, 3 mol %), and 2 mL of toluene were taken
under nitrogen atmosphere and were stirred at room temperature for 30 min.
To this solution, NaOtBu (135 mg, 1.4 mmol) and aryl halide (1.0 mmol) were
added successively. After 15 min, amine (1.2 mmol) was added and the tube
was sealed. The reaction mixture was stirred at 120 °C (oil bath) for 24 h.
Subsequently, the reaction mixture was allowed to cool to room temperature
and EtOAc (4 mL) was added. It was then filtered through a plug of Celite and
was analyzed by GC–MS by using hexadecane as an internal standard. Further
purification of the product was achieved by silica gel column chromatography
[eluent: hexane/EtOAc (95:5)].