Issue 30, 2018

Silylated cyclopentadienes as competent silicon Lewis acid catalysts

Abstract

The synthesis and characterization of silicon Lewis acid complexes that incorporate highly electron-deficient cyclopentadienes is reported. Several pentacarboxycyclopentadienyl and monocarboxytetracyanocyclopentadienyl complexes were prepared. A comparison of their reactivities for catalysis of the allylation of an electron-deficient benzaldehyde was established. The use of a monocarboxytetracyano silylium donor was shown to be effective for the allylation or arylation of a variety of electrophiles via an anion abstraction pathway.

Graphical abstract: Silylated cyclopentadienes as competent silicon Lewis acid catalysts

Supplementary files

Article information

Article type
Edge Article
Submitted
23 May 2018
Accepted
23 Jun 2018
First published
29 Jun 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2018,9, 6406-6410

Silylated cyclopentadienes as competent silicon Lewis acid catalysts

M. A. Radtke and T. H. Lambert, Chem. Sci., 2018, 9, 6406 DOI: 10.1039/C8SC02279H

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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