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Issue 5, 2019
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Palladium(ii) pincer complexes of a C,C,C-NHC, diphosphonium bis(ylide) ligand

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Abstract

A new family of pincer palladium(II) complexes bearing an electron-rich C,C,C-NHC, diphosphonium bis(ylide) ligand of LX2-type was prepared through the dual N-functionalization of 1H-imidazole by (3-bromopropyl)triphenylphosphonium bromide. Selected basic conditions allowed the sequential coordination of the NHC and phosphonium ylide moieties to Pd(II). This strategy led to an original ortho-metallated complex where the Pd center is bonded to four carbon atoms of three different natures: carbenic (sp2), arylic (sp2), and chiral ylidic (sp3). Protonation of the latter afforded NHC, diphosphonium bis(ylide) pincer Pd(II) complexes as a mixture of meso- and dl-diastereomers (de = 50%). The selectivity of C-coordination was rationalized on the basis of DFT calculations, evidencing the quasi-degeneracy of the two diastereomeric forms.

Graphical abstract: Palladium(ii) pincer complexes of a C,C,C-NHC, diphosphonium bis(ylide) ligand

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Article information


Submitted
29 Oct 2018
Accepted
21 Dec 2018
First published
26 Dec 2018

Dalton Trans., 2019,48, 1709-1721
Article type
Paper

Palladium(II) pincer complexes of a C,C,C-NHC, diphosphonium bis(ylide) ligand

R. Taakili, C. Lepetit, C. Duhayon, D. A. Valyaev, N. Lugan and Y. Canac, Dalton Trans., 2019, 48, 1709
DOI: 10.1039/C8DT04316G

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