5 years ago

The Elusive Palladium-Diazo Adduct Captured: Synthesis, Isolation and Structural Characterization of [(ArNHC-PPh2)Pd(η2-N2C(Ph)CO2Et)]

The Elusive Palladium-Diazo Adduct Captured: Synthesis, Isolation and Structural Characterization of [(ArNHC-PPh2)Pd(η2-N2C(Ph)CO2Et)]
Eleuterio Álvarez, Tomás R. Belderrain, Pedro J. Pérez, Manuel R. Fructos, Silvia G. Rull
The first example of a diazo palladium adduct is reported. The complexes [(ArNHC−PPh2)M(η2-N2C(Ph)CO2Et)] (M=Ni, 3; M=Pd, 4; ArNHC−PPh2=3-(2,6-diisopropylphenyl)-1-[(diphenylphosphino)ethyl]imidazol-2-ylidene) were prepared by ligand exchange with styrene-coordinated precursors [(ArNHC−PPh2)M(styrene)] (M=Ni, 1; M=Pd, 2). Complex 4 was fully characterized, including X-ray analyses; this constitutes the first example of a diazo adduct compound with palladium, thereby closing the gap between Groups 8 and 10 regarding this type of compounds. The missing link: All metals from Groups 8 to 10 are known to form adducts with diazo compounds, except for palladium. We report the first example of a Pd-N2CR1R2-type complex, isolated and fully characterized, as well as its role in carbene transfer reactions.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201701362

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