KHF₂: A Mild and Selective Desilylating Agent for Phenol tert-Butyldimethylsilyl (TBDMS) Ethers

Mahesh K. Lakshman*, Fatou A. Tine, Tashrique A. Khandaker, Vikram Basava, Nana B. Agyemang, Michael S. A. Benavidez, Marikone Gaši, Lisa Guerrera, Barbara Zajc*

*Department of Chemistry and Biochemistry, The City College of New York, 160 Convent Avenue, New York, NY 10031, USA, Email: mlakshmanccny.cuny.edu, bzajcccny.cuny.edu

M. K. Lakshman, F. A. Tine, T. A. Khandaker, V. Basava, N. B. Agyemang, M. S. A. Benavidez, M. Gaši, L. Guerrera, B. Zajc, Synlett, 2017, 28, 381-385.

DOI: 10.1055/s-0036-1588350

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Abstract

TBDMS ethers of various phenols have been deprotected at room temperature with KHF₂ in MeOH. Carboxylic esters, labile phenolic acetates and TBDMS ethers of benzylic alcohols were unaffected under these conditions.

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Key Words

deprotection of TBDMS ethers, desilylation, silicon, fluoride, potassium bifluoride

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ID: J60-Y2017