Facile access to silyl-functionalized N-heterocyclic olefins with HSiCl3

Rajendra S. Ghadwal, Sven O. Reichmann, Felix Engelhardt, Diego M. Andrada, Gernot Frenking

Research output: Contribution to journalArticlepeer-review

47 Scopus citations

Abstract

N-heterocyclic olefins (NHOs), IPrCH2 (1) and SIPrCH2 (2) (IPrCH2 = (N(2,6-iPr2C6H3)CH)2CCH2 and SIPrCH2 = (N(2,6-iPr2C6H3)CH2)2CCH2), react with HSiCl3 and afford IPrCH(SiHCl2) (3) and SIPrCH(SiHCl2) (4), respectively. Compounds 3 and 4 have been isolated in almost quantitative yield. Interestingly, treatment of the silylene IPr±SiCl2 with 1 also affords 3, where silylene insertion into a C-H bond is observed. Computational analysis shows a high energy barrier for silylene insertion, therefore a protonation-deprotonation mechanism is more likely.

Original languageEnglish
Pages (from-to)9440-9442
Number of pages3
JournalChemical Communications
Volume49
Issue number82
DOIs
StatePublished - 19 Sep 2013
Externally publishedYes

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