DBU-Mediated Mild and Chemoselective Deprotection of Aryl Silyl Ethers and Tandem Biaryl Ether Formation

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, Email: kimbmsnu.ac.kr

C.-E. Yeom, H. W. Kim, S. Y. Lee, B. M. Kim, Synlett, 2007, 146-150.

DOI: 10.1055/s-2006-958425

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Abstract

With either 1.0 or 0.10 equivalent of DBU, smooth desilylation of various aryl silyl ethers was accomplished selectively in the presence of base-sensitive groups such esters and alkyl silyl ethers. A direct transformation of aryl silyl ethers into biaryl ethers was possible through tandem desilylation and S_NAr reaction with activated aryl fluorides.

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Key Words

chemoselective, desilylation, DBU, biaryl ethers, tert-butyldimethylsilyl ethers, tert-butyldiphenylsilyl ethers

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ID: J60-Y2007-0280