5 years ago

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

Carbodicarbenes: Unexpected π-Accepting Ability during Reactivity with Small Molecules
Shu-kai Liu, Chao-Ping Hsu, Titel Jurca, Gernot Frenking, Chun-Jung Peng, Wei-Chih Shih, Wen-Ching Chen, Yuh-Sheng Wen, Yi-Ping Wang, Tiow-Gan Ong, Diego M. Andrada, Glenn P. A. Yap, Lili Zhao, Chun-Chi Chang
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).

Publisher URL: http://dx.doi.org/10.1021/jacs.7b08031

DOI: 10.1021/jacs.7b08031

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