A novel, chemoselective and efficient microwave-assisted deprotection of silyl ethers with selectfluor.
A novel microwave-assisted, chemoselective and efficient method for the cleavage of silyl ethers (aliphatic and aromatic) catalyzed by Selectfluor is reported. A wide range of TBS-, TIPS-, and TBDPS-protected alkyl silyl ethers can be chemoselectively cleaved in high yield in the presence of aryl silyl ethers. The chemoselective deprotection of phenolic TBS ethers, and not the TIPS- or TBDPS-protected phenolic ethers, and the deprotection of silyl esters were also achieved under these reaction conditions. In addition, the transetherification and etherification of benzylic hydroxy groups in alcoholic solvents is observed.
Shah
Syed Tasadaque A
ST
Centre for Synthesis and Chemical Biology, School of Chemistry and Chemical Biology, UCD Conway Institute, University College Dublin, Belfield, Dublin 4, Ireland.
Singh
Surendra
S
Guiry
Patrick J
PJ