NFSI/KF mediated mild and chemoselective interconversion of aryl TBDMS ethers to their benzene sulfonate

[Display omitted] •Mild interconversion of aryl silyl ether to benzene sulfonate ester.•Stoichiometric use of N-fluorobenzenesulfonimide and potassium fluoride.•Chemoselectivity towards aryl silyl ethers over alkyl silyl ethers.•Electron withdrawing substituent on phenyl ring undergo smooth interconversion. A one pot protocol for the transformation of aryl TBDMS ethers to corresponding benzene sulfonate esters using NFSI (N-flurobenzenesulfonimide)/KF is described. In situ generation of benzenesulfonyl fluoride directs chemoselective cleavage of aryl silyl ethers over alkyl silyl ethers. Electron withdrawing substituent’s on aryl ring provided better yield than donating groups. Protecting groups and sensitive functionalities are well tolerated in this methodology. Thus, commercially available inexpensive reagents, mild reaction conditions and step economy are the advantages of this method.