A Facile, Catalytic, and Environmentally Benign Method for Selective Deprotection of tert-Butyldimethylsilyl Ether Mediated by Phosphomolybdic Acid Supported on Silica Gel

G. D. Kishore Kumar and Sundarababu Baskaran*
Department of Chemistry, Indian Institute of Technology Madras, Chennai 600 036, India sbhaskar@iitm.ac.in
J. Org. Chem., 2005, 70 (11), pp 4520–4523
DOI: 10.1021/jo0502697
Publication Date (Web): April 12, 2005
Copyright © 2005 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

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An environmentally benign PMA supported on SiO2 is found to be an efficient catalyst for the chemoselective deprotection of TBDMS ethers under very mild conditions. Various labile functional groups such as isopropylidene acetal, OTBDPS, OTHP, Oallyl, OBn, alkene, alkyne, OAc, OBz, N-Boc, N-Cbz, N-Fmoc, mesylate, and azide are found to be stable under the reaction conditions. This “truly catalytic” heterogeneous reaction does not require aqueous workup, and the supported catalyst and the solvent can be readily recovered and recycled.

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History

  • Published In Issue May 27, 2005
  • Received February 10, 2005

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