Carbodicarbenes: Unexpected π-Accepting Ability during Reactivity with Small Molecules

Wen Ching Chen, Wei Chih Shih, Titel Jurca, Lili Zhao, Diego M. Andrada, Chun Jung Peng, Chun Chi Chang, Shu Kai Liu, Yi Ping Wang, Yuh Sheng Wen, Glenn P.A. Yap, Chao Ping Hsu, Gernot Frenking, Tiow Gan Ong

Research output: Contribution to journalArticlepeer-review

65 Scopus citations

Abstract

An investigation of carbodicarbenes, the less explored member of the carbenic complex/ligand family has yielded unexpected electronic features and concomitant reactivity. Observed 1,2-addition of E-H bonds (E = B, C, Si) across the carbone central carbon and that of the flanking N-heterocyclic carbene (NHC) fragment, combined with single-crystal X-ray studies of a model Pd complex strongly suggests a significant level of π-accepting ability at the central carbon of the NHC moiety. This feature is atypical of classic NHCs, which are strong σ-donors, with only nominal π-accepting ability. The unanticipated π-acidity is critical for engendering carbodicarbenes with reactivity more commonly observed with frustrated Lewis pairs (FLPs) rather than the more closely related NHCs and cyclic (alkyl)(amino)carbenes (CAACs).

Original languageEnglish
Pages (from-to)12830-12836
Number of pages7
JournalJournal of the American Chemical Society
Volume139
Issue number36
DOIs
StatePublished - 13 Sep 2017

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