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

Xiaoyan Liu; Songlin Zhang

doi:10.1055/s-0030-1259291

LETTER

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: zhangsl@suda.edu.cn;

Abstract

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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.

Key words

catalysis - iron - copper - diaryl ether

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References and Notes

<A NAME="RW15810ST-1A">1a</A> Nicolaou KC. Boddy CNC. Bräse S. Winssinger N. Angew. Chem. Int. Ed. 1999, 38: 2096

<A NAME="RW15810ST-1B">1b</A> Blankenstein J. Zhu J. Eur. J. Org. Chem. 2005, 1949

<A NAME="RW15810ST-1C">1c</A> Frlan R. Kikelj D. Synthesis 2006, 2271

<A NAME="RW15810ST-1D">1d</A> Theil F. Angew. Chem. Int. Ed. 1999, 38: 2345

<A NAME="RW15810ST-1E">1e</A> Ley SV. Thomas AW. Angew. Chem. Int. Ed. 2003, 42: 5400

<A NAME="RW15810ST-2A">2a</A> Paine AJ. J. Am. Chem. Soc. 1987, 109: 1496

<A NAME="RW15810ST-2B">2b</A> Marcoux J.-F. Doye S. Buchwald SL. J. Am. Chem. Soc. 1997, 119: 10539

<A NAME="RW15810ST-2C">2c</A> Palomo C. Oiarbide M. López R. Gómez-Bengoa E. Chem. Commun. 1998, 2091

<A NAME="RW15810ST-2D">2d</A> Buck E. Song ZJ. Tschaen D. Dormer PG. Volante RP. Reider PJ. Org. Lett. 2002, 4: 1623

<A NAME="RW15810ST-2E">2e</A> Cristau H.-J. Cellier PP. Hamada S. Spindler J.-F. Taillefer M. Org. Lett. 2004, 6: 913

<A NAME="RW15810ST-2F">2f</A> Cai Q. Zou B. Ma D. Angew. Chem. 2006, 118: 1298

<A NAME="RW15810ST-2G">2g</A> Chen Y.-J. Chen H.-H. Org. Lett. 2006, 8: 5609

<A NAME="RW15810ST-2H">2h</A> Rao H. Jin Y. Fu H. Jiang Y. Zhao Y. Chem. Eur. J. 2006, 12: 3636

<A NAME="RW15810ST-2I">2i</A> Ouali A. Spindler J.-F. Cristau H.-J. Taillefer M. Adv. Synth. Catal. 2006, 348: 499

<A NAME="RW15810ST-2J">2j</A> Ouali A. Laurent R. Caminade A.-M. Majora J.-P. Taillefer M. J. Am. Chem. Soc. 2006, 128: 15990

<A NAME="RW15810ST-2K">2k</A> Lipshutz BH. Unger JB. Taft BR. Org. Lett. 2007, 9: 1089

<A NAME="RW15810ST-2L">2l</A> Altman RA. Buchwald SL. Org. Lett. 2007, 9: 643

<A NAME="RW15810ST-2M">2m</A> Lv X. Bao W. J. Org. Chem. 2007, 72: 3863

<A NAME="RW15810ST-2N">2n</A> Ouali A. Spindler J.-F. Jutand A. Taillefer M. Adv. Synth. Catal. 2007, 349: 1906

<A NAME="RW15810ST-2O">2o</A> Ouali A. Taillefer M. Organometallics 2007, 26: 65

<A NAME="RW15810ST-2P">2p</A> Benyahya S. Monnier F. Taillefer M. Man MWC. Bied C. Ouazzani F. Adv. Synth. Catal. 2008, 350: 2205

<A NAME="RW15810ST-2Q">2q</A> Monnier F. Taillefer M. Angew. Chem. Int. Ed. 2008, 47: 3096

<A NAME="RW15810ST-2R">2r</A> Zhang Q. Wang D. Wang X. Ding K. J. Org. Chem. 2009, 74: 7187

<A NAME="RW15810ST-2S">2s</A> Liu Y.-H. Li G. Yang L.-M. Tetrahedron Lett. 2009, 50: 343

<A NAME="RW15810ST-2T">2t</A> Tye JW. Weng Z. Giri R. Hartwig JF. Angew. Chem. Int. Ed. 2010, 49: 2185

For general reviews, see:

<A NAME="RW15810ST-3A">3a</A> Ley SV. Thomas AW. Angew. Chem. Int. Ed. 2003, 42: 5400

<A NAME="RW15810ST-3B">3b</A> Beletskaya IP. Cheprakov AV. Coord. Chem. Rev. 2004, 248: 2337

<A NAME="RW15810ST-3C">3c</A> Evano G. Blanchard N. Toumi M. Chem. Rev. 2008, 108: 3054

<A NAME="RW15810ST-3D">3d</A> Monnier F. Taillefer M. Angew. Chem. Int. Ed. 2009, 48: 6954

<A NAME="RW15810ST-4A">4a</A> Tamura M. Kochi JK. J. Am. Chem. Soc. 1971, 93: 1487

<A NAME="RW15810ST-4B">4b</A> Tamura M. Kochi JK. Synthesis 1971, 303

<A NAME="RW15810ST-4C">4c</A> Tamura M. Kochi JK. J. Organomet. Chem. 1971, 31: 289

For recent contributions on iron catalysis, see:

<A NAME="RW15810ST-5A">5a</A> Plietker B. Angew. Chem. Int. Ed. 2006, 45: 6053

<A NAME="RW15810ST-5B">5b</A> Komeyama K. Morimoto T. Takaki K. Angew. Chem. Int. Ed. 2006, 45: 2938

<A NAME="RW15810ST-5C">5c</A> Gelalcha FG. Bitterlich B. Anilkumar G. Tse MK. Beller M. Angew. Chem. Int. Ed. 2007, 46: 7293

<A NAME="RW15810ST-5D">5d</A> Taillefer M. Xia N. Ouali A. Angew. Chem. Int. Ed. 2007, 46: 934

<A NAME="RW15810ST-5E">5e</A> Jadhav VH. Dumbre DK. Phapale VB. Borate HB. Wakharkar RD. Catal. Commun. 2007, 8: 65

<A NAME="RW15810ST-5F">5f</A> Correa A. Bolm C. Angew. Chem. Int. Ed. 2007, 46: 8862

<A NAME="RW15810ST-5G">5g</A> Guo D. Huang H. Xu J. Jiang H. Liu H. Org. Lett. 2008, 10: 4513

<A NAME="RW15810ST-5H">5h</A> Du Y. Chang J. Reiner J. Zhao K. J. Org. Chem. 2008, 73: 2007

<A NAME="RW15810ST-5I">5i</A> Correa A. Bolm C. Adv. Synth. Catal. 2008, 350: 391

<A NAME="RW15810ST-5J">5j</A> Bistri O. Correa A. Bolm C. Angew. Chem. 2008, 120: 596

<A NAME="RW15810ST-5K">5k</A> Bonnamour J. Bolm C. Org. Lett. 2008, 10: 2665

<A NAME="RW15810ST-5L">5l</A> Correa A. Carril M. Bolm C. Angew. Chem. Int. Ed. 2008, 47: 2880

<A NAME="RW15810ST-5M">5m</A> Correa A. Carril M. Bolm C. Chem. Eur. J. 2008, 14: 10919

<A NAME="RW15810ST-5N">5n</A> Wang Z. Zhang Y. Fu H. Jiang Y. Zhao Y. Org. Lett. 2008, 10: 1863

<A NAME="RW15810ST-5O">5o</A> Yao B. Liang Z. Niu T. Zhang Y. J. Org. Chem. 2009, 74: 4630

<A NAME="RW15810ST-5P">5p</A> Teo Y.-C. Adv. Synth. Catal. 2009, 351: 720

<A NAME="RW15810ST-5Q">5q</A> Mao J. Xie G. Zhan J. Hua Q. Shi D. Adv. Synth. Catal. 2009, 351: 1268

<A NAME="RW15810ST-5R">5r</A> Qiu J.-W. Zhang X.-G. Tang R.-Y. Zhong P. Li J.-H. Adv. Synth. Catal. 2009, 351: 2319

<A NAME="RW15810ST-5S">5s</A> Wu J.-R. Lin C.-H. Lee C.-F. Chem. Commun. 2009, 4450

<A NAME="RW15810ST-5T">5t</A> Li P. Zhang Y. Wang L. Chem. Eur. J. 2009, 15: 2045

<A NAME="RW15810ST-5U">5u</A> Ku X. Huang H. Jiang H. Liu H. J. Comb. Chem. 2009, 11: 338

<A NAME="RW15810ST-5V">5v</A> Swapna K. Kumar AV. Reddy VP. Rao KR. J. Org. Chem. 2009, 74: 7514

<A NAME="RW15810ST-5W">5w</A> Liang Z. Hou W. Du Y. Zhang Y. Pan Y. Mao D. Zhao K. Org. Lett. 2009, 11: 4978

<A NAME="RW15810ST-5X">5x</A> Lee HW. Chan ASC. Kwong FY. Tetrahedron Lett. 2009, 50: 5868

<A NAME="RW15810ST-5Y">5y</A> Xu X. Liu J. Liang L. Li H. Li Y. Adv. Synth. Catal. 2009, 351: 2599

For pertinent reviews on Fe-catalyzed coupling reactions, see:

<A NAME="RW15810ST-6A">6a</A> Sherry BD. Fürstner A. Acc. Chem. Res. 2008, 41: 1500

<A NAME="RW15810ST-6B">6b</A> Correa A. Mancheńo OG. Bolm C. Chem. Soc. Rev. 2008, 37: 1108

<A NAME="RW15810ST-6C">6c</A> Czaplik WM. Mayer M. Cvengros J. von Wangelin AJ. ChemSusChem 2009, 2: 396

<A NAME="RW15810ST-7">7</A> Buchwald SL. Bolm C. Angew. Chem. Int. Ed. 2009, 48: 5586

<A NAME="RW15810ST-8A">8a</A> Wang Z. Fu H. Jiang Y. Zhao Y. Synlett 2008, 2540

<A NAME="RW15810ST-8B">8b</A> Taillefer M. Xia N. Ouali A. US 60/818,334, 2006 WO 001836, 2007

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.

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