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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.

SUBMITTER: Radtke MA 

PROVIDER: S-EPMC6115689 | biostudies-other | 2018 Aug

REPOSITORIES: biostudies-other

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Silylated cyclopentadienes as competent silicon Lewis acid catalysts.

Radtke M Alex MA   Lambert Tristan H TH  

Chemical science 20180629 30

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 electrophi  ...[more]