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.
see article for more examples
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 SNAr reaction with activated aryl fluorides.
see article for more reactions
chemoselective, desilylation, DBU, biaryl ethers, tert-butyldimethylsilyl ethers, tert-butyldiphenylsilyl ethers