Highly Efficient C-O Cross-Coupling Reactions with Unactivated Halides by Ligandless, Heterogeneous Raney Ni-Al Alloy/Copper (I) Salts

Li-Wen Xu; Chun-Gu Xia; Jing-Wei Li; Xiao-Xue Hu

doi:10.1055/s-2003-41476

LETTER

Highly Efficient C-O Cross-Coupling Reactions with Unactivated Halides by Ligandless, Heterogeneous Raney Ni-Al Alloy/Copper (I) Salts

Li-Wen Xu, Chun-Gu Xia*, Jing-Wei Li, Xiao-Xue Hu
State key Laboratory of Oxo Synthesis & Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, 730000, P R China
Fax: +86(931)8277088; e-Mail: cgxia@ns.lzb.ac.cn;

Abstract

All articles of this category

Abstract

A general, novel, ligandless and efficient method was developed for the Raney Ni-Al alloy/copper co-catalyzed formation of diaryl ethers by C-O cross-coupling reaction from aryl iodides, bromides, and even aryl chlorides with phenols.

Key words

copper - Raney Ni-Al alloy - cross-coupling - phenols - ligandless

Full Text

References

<A NAME="RU15803ST-1A">1a</A> Mino T. Shirae Y. Sakamoto M. Fujita T. Synlett 2003, 882

<A NAME="RU15803ST-1B">1b</A> Jonckers THM. Maes BU. Lemiere GLF. Rombouts G. Pieters L. Haemers A. Dommisse RA. Synlett 2003, 615

<A NAME="RU15803ST-1C">1c</A> Gonthier E. Breinbauer R. Synlett 2003, 1049

<A NAME="RU15803ST-1D">1d</A> Iyer S. Jayanthi A. Synlett 2003, 1125

<A NAME="RU15803ST-1E">1e</A> Nicolaou KC. Christopher NCB. J. Am. Chem. Soc. 2002, 124: 10451

<A NAME="RU15803ST-1F">1f</A> Strurmer R. Angew. Chem. Int. Ed. 1999, 38: 3307

<A NAME="RU15803ST-1G">1g</A> Wolfe JP. Wagaw S. Marcoux JF. Buchwald SL. Acc. Chem. Res. 1998, 31: 805

<A NAME="RU15803ST-2A">2a</A> Pello’n RF. Carrasco R. Milia’n V. L. Synth.Commun. 1995, 25: 1077

<A NAME="RU15803ST-2B">2b</A> Theil F. Angew. Chem. Int. Ed. 1999, 38: 2345 ; and references cited therein

For examples of biologically important diaryl ethers, see:

<A NAME="RU15803ST-3A">3a</A> Islas-Gonzalez G. Bois-Choussy MZ. J. Org. Biomol. Chem. 2003, 1: 30

<A NAME="RU15803ST-3B">3b</A> Evans DA. DeVries MK. In Glycopeptide Antibiotics, Drugs and the Pharmaceutical Sciences 63: Nagarajan R. Marcel Decker; New York: 1994. p.63

<A NAME="RU15803ST-3C">3c</A> Eicher T. Fey S. Puhl W. Buchel E. Speicher A. Eur. J. Org. Chem. 1998, 877

<A NAME="RU15803ST-3D">3d</A> Iyoda M., Sakaitani M., Otsuka, H., Oda M.; Tetrahedron Lett.; 1985, 26: 4777

<A NAME="RU15803ST-3E">3e</A> Evans DA. Wood MR. Trotter BW. Richardson TI. Barrow JC. Katz JL. Angew. Chem. Int. Ed. 1998, 37: 2700

<A NAME="RU15803ST-3F">3f</A> Evans DA. Dinsmore CJ. Watson PS. Wood MR. Richardson TI. Trotter BW. Katz JL. Angew. Chem. Int. Ed. 1998, 37: 2704

<A NAME="RU15803ST-3G">3g</A> Zhang AJ. Burgess K. Angew. Chem. Int. Ed. 1999, 38: 634

<A NAME="RU15803ST-4A">4a</A> Ullmann F. Chem. Ber. 1904, 37: 853

<A NAME="RU15803ST-4B">4b</A> Lindley J. Tetrahedron 1984, 40: 1433

<A NAME="RU15803ST-4C">4c</A> Chan DMT. Winters MP. Monacoand KL. Wang R. Tetrahedron Lett. 1998, 39: 2933

<A NAME="RU15803ST-5">5</A> Mann G. Hartwig JF. Tetrahedron Lett. 1997, 38: 8005

<A NAME="RU15803ST-6">6</A> Aranyos A. Old DW. Kiyomori A. Wolfe JP. Sadighi JP. Buchwald SL. J. Am. Chem. Soc. 1999, 121: 4369

<A NAME="RU15803ST-7A">7a</A> Goodbrand HB. Hu NX. J. Org. Chem. 1999, 64: 670

<A NAME="RU15803ST-7B">7b</A> Fagan PJ. Hauptman E. Shapiro R. Casalnuovo A. J. Am. Chem. Soc. 2002, 122: 5043

<A NAME="RU15803ST-8">8</A> Marcoux JF. Doye S. Buchwald SL. J. Am. Chem. Soc. 1997, 119: 10539

<A NAME="RU15803ST-9A">9a</A> Evans DA. Katz JL. West TR. Tetrahedron Lett. 1998, 39: 2937

<A NAME="RU15803ST-9B">9b</A> Decicco CP. Song Y. Evans DA. Org. Lett. 2001, 3: 1029

<A NAME="RU15803ST-9C">9c</A> Lam PYS. Vincent G. Clark C. Deudon S. Jadhav PK. Tetrahedron Lett. 2001, 42: 3415

<A NAME="RU15803ST-9D">9d</A> Lam PYS. Vincent G. Bonne D. Clark CG. Tetrahedron Lett. 2003, 44: 4927

<A NAME="RU15803ST-10A">10a</A> Gujadhur RK. Bates CG. Venkataraman D. Org. Lett. 2001, 3: 4315

<A NAME="RU15803ST-10B">10b</A> Gujadhur R. Venkataraman D. Synth. Commun. 2001, 31: 1077

<A NAME="RU15803ST-10C">10c</A> Li F. Wang Q. Ding Z. Tao F. Org. Lett. 2003, 5: 2865

<A NAME="RU15803ST-10D">10d</A> Wipf P. Lynch SM. Org. Lett. 2003, 5: 1155

<A NAME="RU15803ST-10E">10e</A> He H. Wu YJ. Tetrahedron Lett 2003, 44: 3445

<A NAME="RU15803ST-11A">11a</A> Wolfe JP. Buchwald SL. J. Am. Chem. Soc. 1997, 119: 6054

<A NAME="RU15803ST-11B">11b</A> Bolm C. Hildebrand JP. Rudolph J. Synthesis 2000, 911

<A NAME="RU15803ST-11C">11c</A> Lipshutz BH. Ueda H. Angew. Chem. Int. Ed. 2000, 39: 4492

<A NAME="RU15803ST-11D">11d</A> Desmarets C. Scheneider R. Fort Y. J. Org. Chem. 2002, 67: 3029

<A NAME="RU15803ST-11E">11e</A> Tasler S. Lipshutz BH. J. Org. Chem. 2003, 68: 1190 ; and references cited therein

<A NAME="RU15803ST-12A">12a</A> Mukumoto M. Mashimo T. Tsuzuki H. Tsukinoki T. Uezu N. Mataka S. Tashiro M. Kakinami TT. J. Chem. Res., Synop. 1995, 412

<A NAME="RU15803ST-12B">12b</A> Liu GB. Tsukinoki T. Kanda T. Mitoma Y. Tashiro M. Tetrahedron Lett. 1998, 39: 5991

<A NAME="RU15803ST-12C">12c</A> Ishimoto K. Mitoma Y. Nagashima S. Tashiro H. Surya Prakash GK. Olah GA. Tashiro M. Chem. Commun. 2003, 514

Typical Experimental Procedure. An oven-dried resealable Schlenk tube was fitted with a rubber septum and was cooled to room temperature under N₂ purge. The septum was removed, and the tube was charged with CuI (10 mol%), 10-50 mg Raney Ni-Al alloy, K₂CO₃ (2.0 mmol), aryl halides (1.0mmol), and phenols (1.2-1.4 mmol). The tube was capped with the septum and purged with N₂, and then dioxane(2ml) was added through the septum. The reaction mixture was stirred at 110 °C for 12-24 h (reaction times were not optimized). The reaction mixture was allowed to cool to room temperature and then diluted with ether and poured into a separating funnel. The mixture was washed with 1 M NaOH and brine, and then the organic fraction was dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude material was purified by flash chromatography on silical gel.

<A NAME="RU15803ST-14A">14a</A> Moroz AA. Shvartsberg MS. Russ. Chem. Rev. 1974, 43: 679

<A NAME="RU15803ST-14B">14b</A> Lindley J. Tetrahedron 1984, 40: 1433

<A NAME="RU15803ST-15">15</A> Lituak VV. Shein SM. Zh. Org. Khim. 1974, 2373

<A NAME="RU15803ST-16">16</A> Aaten HL. van Koten G. Grove DM. Kuilman T. Piekstra OG. Hulshof LA. Sheldon RA. Tetrahedron 1989, 45: 5565

All the products were identified by NMR and GC-MS (Agilent 6890N GC/5973N MS, HP-5MS). Selected data for the product of entry 13: ¹H NMR (300 MHz, CDCl₃): 7.86 (d, J = 8.7 Hz, 2 H), 7.41-6.92 (18 H), 6.81 (d, J = 8.4 Hz, 2 H); ¹³C NMR (300 MHz, CDCl₃): 157.45, 152.54, 134.19, 129.705, 129.58, 129.26, 128.01, 126.55, 125.75, 124.59, 123.19, 122.64, 119.27, 118.88.