Synlett 2011(2): 268-272  
DOI: 10.1055/s-0030-1259291
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Efficient Iron/Copper-Cocatalyzed O-Arylation of Phenols with Bromoarenes

Xiaoyan Liu, Songlin Zhang*
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science,, Suzhou University, Dushu Lake Campus, Suzhou, 215123, P. R. of China
Fax: +86(512)65880352; e-Mail: [email protected];
Further Information

Publication History

Received 2 October 2010
Publication Date:
23 December 2010 (online)

Abstract

Low catalytic amount CuI and Fe(acac)3 were found to effectively promote the C-O cross-coupling reaction in the presence of K2CO3 as the base. A serious of diaryl ethers with different substitutents can be synthesized in good to excellent yields. This efficient and economic method is attractive for applications on an industrial scale.

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9

General Procedure for the Synthesis of Diaryl Ethers
A Schlenk tube equipped with a magnetic stir bar was charged with K2CO3 (138 mg, 1 mmol), Fe(acac)3 (3.5 mg, 2% mol), CuI (1.0 mg, 1% mol), and the phenol (0.5 mmol) in anhyd DMF (0.8 mL). The reaction mixture was heated at 135 ˚C. After being stirred at this temperature for 12 h, the mixture was cooled to r.t. and diluted with Et2O. The resulting suspension was directly filtered through a pad of Celite, and the filtrate was washed with sat. NaCl and dried over anhyd Na2SO4. The organic phase was concentrated, and the crude mixtures were purified by column chroma-tography on silica gel (300-400 mesh) using PE-EtOAc solvent mixture as the eluent. Diphenyl Ether (3a)
¹H NMR (400 MHz, CDCl3): δ = 7.33 (t, J = 7.6 Hz, 4 H), 7.10 (t, J = 7.2 Hz, 2 H), 7.01 (d, J = 7.8 Hz, 4 H). ¹³C NMR (100 MHz, CDCl3): δ = 157.70, 130.19, 123.70, 119.34.
N -(4-Phenoxyphenyl)acetamide (Table 2, Entry 6) ¹H NMR (400 MHz, CDCl3): δ = 7.45 (d, J = 8.8 Hz, 2 H), 7.42 (s, 1 H), 7.31 (t, J = 7.8 Hz, 2 H), 7.08 (t, J = 7.4 Hz, 1 H), 6.97 (d, J = 7.8 Hz, 4 H), 2.17 (s, 3 H). ¹³C NMR (100 MHz, CDCl3): δ = 169.25, 157.87, 153.82, 133.90, 130.15, 123.51, 122.29, 119.92, 118.82, 24.71.
1- tert -Butyl-2-phenoxybenzene (Table 2, Entry 8) ¹H NMR (400 MHz, CDCl3): δ = 7.42 (d, J = 7.7 Hz, 1 H), 7.33 (t, J = 7.8 Hz, 2 H), 7.15 (t, J = 7.0 Hz, 1 H), 7.10-7.05 (m, 2 H), 6.99 (d, J = 8.0 Hz, 2 H), 6.84 (d, J = 7.9 Hz, 1 H), 1.44 (s, 9 H). ¹³C NMR (100 MHz, CDCl3): δ = 158.24, 156.30, 141.40, 130.13, 127.67, 127.57, 123.68, 123.08, 120.65, 119.13, 35.24, 30.62.
4-(4-Methoxyphenoxy)aniline (Table 2, Entry 15) ¹H NMR (400 MHz, CDCl3): δ = 6.90 (d, J = 8.8 Hz, 2 H), 6.84-6.81 (m, 4 H), 6.65 (d, J = 8.4 Hz, 2 H) 3.78 (s, 3 H). ¹³C NMR (100 MHz, CDCl3): δ = 155.43, 152.46, 150.46, 142.47, 120.37, 119.49, 116.66, 115.08, 56.09
3-(4-Methoxyphenoxy)pyridine (Table 2, Entry 23) ¹H NMR (400 MHz, CDCl3): 8.19 (d, J= 4.9 Hz, 1 H,) 7.66 (t, J = 7.7 Hz, 1 H), 7.08 (d, J= 9.1 Hz, 2 H), 6.97 (d, J = 6.0 Hz, 1 H), 6.93 (d, J = 9.1 Hz, 2 H), 6.86 (s, 1 H), 3.82 (s, 3 H).¹³C NMR (100 MHz, CDCl3): 164.64, 156.93, 148.08, 147.73, 139.69, 122.77, 118.47, 115.14, 111.42, 55.95.