Use of catalytic fluoride under neutral conditions for cleaving silicon-oxygen bonds

Anthony M. Dilauro, Wanji Seo, Scott T. Phillips

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

This Article describes the development of conditions for cleaving silicon-oxygen bonds using catalytic quantities of fluoride at neutral pH in mixed organic-aqueous solutions that contain buffer. A variety of silicon protecting groups can be removed under these conditions, which show tolerance for acid- and base-sensitive groups. A modified procedure also is presented using catalytic fluoride in anhydrous dimethyl sulfoxide-methanol, which generates primarily volatile silicon byproducts.

Original languageEnglish (US)
Pages (from-to)7352-7358
Number of pages7
JournalJournal of Organic Chemistry
Volume76
Issue number18
DOIs
StatePublished - Sep 16 2011

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Silicon
Fluorides
Oxygen
Dimethyl Sulfoxide
Byproducts
Methanol
Buffers
Acids

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Dilauro, Anthony M. ; Seo, Wanji ; Phillips, Scott T. / Use of catalytic fluoride under neutral conditions for cleaving silicon-oxygen bonds. In: Journal of Organic Chemistry. 2011 ; Vol. 76, No. 18. pp. 7352-7358.
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Use of catalytic fluoride under neutral conditions for cleaving silicon-oxygen bonds. / Dilauro, Anthony M.; Seo, Wanji; Phillips, Scott T.

In: Journal of Organic Chemistry, Vol. 76, No. 18, 16.09.2011, p. 7352-7358.

Research output: Contribution to journalArticle

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