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| LETTER | Synlett 2007: 0146-0150
DOI: 10.1055/s-2006-958425 |
© Georg Thieme Verlag Stuttgart · New York
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DBU-Mediated Mild and Chemoselective Deprotection of Aryl Silyl Ethers and Tandem Biaryl Ether Formation
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| Chang-Eun Yeom, Hye Won Kim, So Young Lee, B. Moon Kim* |
Department of Chemistry, College of Natural Sciences, Seoul National University, Seoul 151-747, Korea
Fax: +82(2)8727505; e-Mail: kimbm@snu.ac.kr;
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Received
21 September 2006 |
Abstract
An efficient method for the selective cleavage of aryl silyl ethers is established using 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). With either 1.0 or 0.10 equivalent of DBU, smooth desilylation of various aryl silyl ethers was accomplished selectively in the presence of alkyl silyl ethers and other base-sensitive groups such as acetate and ester. In addition, direct transformation of aryl silyl ethers into biaryl ethers using a catalytic amount of DBU was possible through tandem desilylation and SNAr reaction with activated aryl fluorides. Key words
chemoselective - catalytic - desilylation - DBU - biaryl ether
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