Selective Deprotection of tert-Butyldimethylsilyl Ethers Using Nafion-H®/Sodium Iodide (or Bromodimethylsulfonium Bromide) in Methanol

Abstract

Catalytic amounts of bromodimethyl sulfonium bromide, or Nafion-H along with NaI (1 equiv.), in methanol cleave a variety of TBDMS ethers readily in high yields. Alkyl TBDMS ethers react more readily and selectively compared to phenolic TBDMS ethers, benzyl, and methyl ethers.

Keywords:

• TBDMS ethers
• Selective deprotection
• Nafion-H/NaI
• Bromodimethyl sulphonium bromide

Acknowledgment

We thank the Department of Science and Technology, New Delhi for financial assistance (Project No. SP/S1/G07/97). One of us (SR) thanks CSIR for a Senior Research Fellowship. We also thank Profs. G. A. Olah and G. K. S. Prakash for the gift of Nafion-K.