Mechanism of dehydrogenative condensation of (oborylphenyl) hydrosilanes with methanol

László Könczöl, Atsushi Kawachi, D. Szieberth

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

The dehydrogenative condensation of hydrosilanes and alcohols is a facile way of protecting alcohols in chemical synthesis. Recently, Kawachi and co-workers combined the B(C 6F 5) 3 catalyst and the hydrosilyl group in one molecule, enabling the coupling reaction to take place at room temperature without additional catalyst. In this paper, the mechanism of the reaction of this novel protecting group with methanol is explored using computational techniques. A stepwise reaction pathway was found to be preferred to the concerted one. The mechanism can be interpreted using the FLP framework. In the preferred pathway, the activation of the Si-H and O-H bonds happens simultaneously. While the hydride-like hydrogen on the Si atom is activated by the Lewis acidic boron site, the O-H bond is activated by the π-system of one of the mesityl substituents on the boron atom. Further calculations show that, by changing the acidity of the Lewis acidic site, the activation barrier of the reaction can be tuned.

Original languageEnglish
Pages (from-to)120-125
Number of pages6
JournalOrganometallics
Volume31
Issue number1
DOIs
Publication statusPublished - Jan 9 2012

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Boron
Methanol
Condensation
methyl alcohol
condensation
Chemical activation
Alcohols
Atoms
Catalysts
Acidity
Hydrides
Hydrogen
boron
alcohols
activation
catalysts
Molecules
acidity
hydrides
atoms

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Inorganic Chemistry

Cite this

Mechanism of dehydrogenative condensation of (oborylphenyl) hydrosilanes with methanol. / Könczöl, László; Kawachi, Atsushi; Szieberth, D.

In: Organometallics, Vol. 31, No. 1, 09.01.2012, p. 120-125.

Research output: Contribution to journalArticle

Könczöl, László ; Kawachi, Atsushi ; Szieberth, D. / Mechanism of dehydrogenative condensation of (oborylphenyl) hydrosilanes with methanol. In: Organometallics. 2012 ; Vol. 31, No. 1. pp. 120-125.
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