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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 (free Supporting Information)


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


ID: J60-Y2017