Please use this identifier to cite or link to this item: https://doi.org/10.1021/om101169x
Title: Reactivity differences of palladium(II) dimers bearing heterocyclic carbenes with two, one, or no α-nitrogen atoms toward isocyanides
Authors: Han, Y. 
Yuan, D.
Teng, Q.
Huynh, H.V. 
Issue Date: 14-Mar-2011
Citation: Han, Y., Yuan, D., Teng, Q., Huynh, H.V. (2011-03-14). Reactivity differences of palladium(II) dimers bearing heterocyclic carbenes with two, one, or no α-nitrogen atoms toward isocyanides. Organometallics 30 (5) : 1224-1230. ScholarBank@NUS Repository. https://doi.org/10.1021/om101169x
Abstract: Pd(II) dimers [PdI2(rNHC)]2 (1a,b) of pyrazole-based remote N-heterocyclic carbenes (rNHCs) have been synthesized through oxidative addition of 4-iodopyrazolium iodides (A, B) to [Pd2(dba) 3]. Reaction of 1a with aromatic (CN-Xyl) or aliphatic (CN-Cy) isocyanides led to the template-assisted formation of novel Pd(II) dimers 8 and 9 bearing betainic C-imino ligands via isocyanide insertion into Pd-C rNHC bonds and subsequent dimerization. In contrast, both isocyanides reacted with the dimers [PdI2(Me2-indy)]2 (2) and [PdI2(Me2-bimy)]2 (3) bearing indazolin-3-ylidenes and benzimidazolin-2-ylidenes with formation of mononuclear mixed carbene/isocyanide complexes 4-7. Notably, only dimer 8 underwent further bridge cleavage with excess isocyanide, yielding the mixed C-imino/CN-Xyl complex 10, while dimer 9 remained intact. These results highlight the uniquely different reactivities of complexes with carbenes having no α-nitrogen versus those with one or two α-nitrogen atoms, as a result of their decreasing donor abilities. © 2011 American Chemical Society.
Source Title: Organometallics
URI: http://scholarbank.nus.edu.sg/handle/10635/94690
ISSN: 02767333
DOI: 10.1021/om101169x
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