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DOI: 10.1055/s-0029-1216551
Copper/Aluminum Hydrotalcite Catalyzed O-Arylation of Phenols/Alcohols with Aryl Halides
Contributor(s):Yasuhiro Uozumi, Yoichi M. A. Yamada, Hidetoshi OhtaIndian Institute of Chemical Technology, Hyderabad, India
Efficient Catalytic Activity of Copper/Aluminum Hydrotalcite in Diaryl Ether Synthesis
Synthesis 2009, 483-487
Publication History
Publication Date:
22 April 2009 (online)
Key words
hydrotalcite - phenols - copper
Significance
Copper/aluminum hydrotalcite (Cu/Al-HF, Cu:Al = 2.5:1, 34.94 atm% Cu) was found to catalyze O-arylation of various phenols and alcohols 2 with aryl halides 1. Thus, the reaction of 1 with 2 was carried out in the presence of Cu/Al-HF and K2CO3 in DMF to give the corresponding aryl ethers 3 in 47-97% yield. The Cu/Al-HF catalyst was recovered by filtration and reused four times with slight loss of catalytic activity.
Comment
The Cu/Al-HF catalyst has been developed by Velu and Swamy (S. Velu, C. S. Swamy Appl. Catal., A: Gen. 1996, 145, 141; see also: M. L. Kantam et al. Org. Lett. 2008, 10, 2979). The authors reported the Cu/Al-HT catalyzed N-arylation of amines with aryl chlorides (P. R. Likhar, R. Arundhathi, M. L. Kantam Tetrahedron Lett. 2007, 48, 3911) and the copper fluoroapatite catalyzed N-arylation of N-heterocycles with chloro- and fluoroarenes (B. M. Choudary, C. Sridhar, M. L. Kantam, G. T. Venkanna, B. Sreedhar J. Am. Chem. Soc. 2005, 127, 9948).