Efficient Catalytic Activity
of Copper/Aluminum Hydrotalcite in Diaryl Ether Synthesis

B. Sreedhar; R. Arundhathi; M. Amarnath Reddy; M. Lakshmi Kantam

doi:10.1055/s-0028-1083304

PAPER

Efficient Catalytic Activity of Copper/Aluminum Hydrotalcite in Diaryl Ether Synthesis

B. Sreedhar*, R. Arundhathi, M. Amarnath Reddy, M. Lakshmi Kantam
Indian Institute of Chemical Technology, Inorganic and Physical Chemistry Division, Hyderabad 500 007, India
Fax: +91(40)2716092; e-Mail: sreedharb@iict.res.in;

Abstract

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Abstract

A simple copper/aluminum hydrotalcite (Cu/Al-HT) catalyzed arylation of phenols with aryl iodides afforded the corresponding diaryl ethers in moderate to excellent yields. This ligand-free Cu/Al-HT catalyzed coupling of aryl iodides with phenols resulted in high yields of diaryl ethers in the absence of an additive. The catalyst was quantitatively recovered from the reaction by simple filtration and reused for a number of cycles.

Key words

hydrotalcite - copper - coupling - phenol - reusable catalyst

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For reviews, see:

<A NAME="RP09108SS-1A">1a</A> Nicolaou KC. Boddy CNC. Brase S. Winssinger N. Angew. Chem. Int. Ed. 1999, 38: 2096 ; Angew. Chem. 1999, 111, 2230

<A NAME="RP09108SS-1B">1b</A> Blankenstein J. Zhu J. Eur. J. Org. Chem. 2005, 1949

<A NAME="RP09108SS-1C">1c</A> Frlan R. Kikelj D. Synthesis 2006, 2271

<A NAME="RP09108SS-2A">2a</A> Evans DA. Dinsmore CJ. Watson PS. Wood MR. Richardson TI. Trotter BW. Katz JL. Angew. Chem. Int. Ed. 1998, 37: 2704 ; Angew. Chem. 1998, 110, 2868

<A NAME="RP09108SS-2B">2b</A> Nicolaou KC. Natarajan S. Li H. Jain NF. Huges R. Solomon ME. Ramanujulu JM. Boddy CNC. Takayanagi M. Angew. Chem. Int. Ed. 1998, 37: 2708 ; Angew. Chem. 1998, 110, 2872,

<A NAME="RP09108SS-3">3</A> Deng H. Jung JK. Liu T. Kuntz KW. Snapper ML. Hoveyda AH. J. Am. Chem. Soc. 2003, 125: 9032

<A NAME="RP09108SS-4A">4a</A> Ullmann F. Sponagel P. Chem. Ber. 1905, 38: 2211

<A NAME="RP09108SS-4B">4b</A> Ullmann F. Chem. Ber. 1904, 37: 853

<A NAME="RP09108SS-4C">4c</A> Ullmann F. Chem. Ber. 1903, 36: 2382

<A NAME="RP09108SS-4D">4d</A> Ullmann F. Chem. Ber. 1901, 34: 2174

<A NAME="RP09108SS-4E">4e</A> Ley S. Thomas AW. Angew. Chem. Int. Ed. 2003, 42: 5400

<A NAME="RP09108SS-4F">4f</A> Kunz K. Scholtz U. Ganzer D. Synlett 2003, 2428

<A NAME="RP09108SS-4G">4g</A> Sawyer JS. Tetrahedron 2000, 56: 5045

<A NAME="RP09108SS-5">5</A> Mann G. Hartwig JF. Tetrahedron Lett. 1997, 46: 8005

<A NAME="RP09108SS-6">6</A> Evans DA. Katz JL. West TR. Tetrahedron Lett. 1998, 30: 2053

<A NAME="RP09108SS-7">7</A> Chan DMT. Monaco KL. Wang RP. Winters MP. Tetrahedron Lett. 1998, 39: 2933

<A NAME="RP09108SS-8A">8a</A> Bistri O. Correa A. Bolm C. Angew. Chem. Int. Ed. 2008, 47: 586

<A NAME="RP09108SS-8B">8b</A> Burgos CH. Barder TE. Huang X. Buchwald SL. Angew Chem. Int. Ed. 2006, 45: 4321

<A NAME="RP09108SS-9">9</A> Sels F. De Vos DE. Jacobs PA. Catal. Rev. 2001, 43: 443

<A NAME="RP09108SS-10">10</A> Likhar PR. Arundhathi R. Kantam ML. Tetrahedron Lett. 2007, 48: 3911

<A NAME="RP09108SS-11">11</A> Ouali A. Spindler JF. Talifer M. Adv. Synth. Catal. 2006, 118: 1298

<A NAME="RP09108SS-12">12</A> Chen Y.-J. Chen H.-H. Org. Lett. 2006, 8: 5609

<A NAME="RP09108SS-13">13</A> Li F. Wang Q. Ding Z. Tao G. Org. Lett. 2003, 5: 2169

<A NAME="RP09108SS-14">14</A> Evans D. A. Katz J. L. West T. R. Tetrahedron Lett. 1998, 39: 2937

<A NAME="RP09108SS-15">15</A> Yeom C.-E. Kim H. W. Lee S. Y. Kim B. Synlett 2007, 146