Palladium(ii)-Acetylacetonato Complexes with Mesoionic Carbenes: Synthesis, Structures and Their Application in the Suzuki-Miyaura Cross Coupling Reaction
Institut für Chemie und Biochemie, Anorganische Chemie, Freie Universität Berlin, Fabeckstraße 34-36, Berlin D-14195, Germany
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Academic Editors: James Crowley and Derek J. McPhee
Molecules 2016, 21(11), 1561; https://doi.org/10.3390/molecules21111561
Received: 20 September 2016 / Revised: 2 November 2016 / Accepted: 12 November 2016 / Published: 17 November 2016
(This article belongs to the Special Issue Recent Advances in CuAAC Click Chemistry)
A series of novel palladium(ii) acetylacetonato complexes bearing mesoionic carbenes (MICs) have been synthesized and characterized. The synthesis of the complexes of type (MIC)Pd(acac)I (MIC = 1-mesityl-3-methyl-4-phenyl-1,2,3-triazol-5-ylidene (1), 1,4-(2,4,6-methyl)-phenyl-3-methyl-1,2,3-triazol-5-ylidene (2), 1,4-(2,6-diisopropyl)-phenyl-3-methyl-1,2,3-triazol-5-ylidene (3); acac = acetylacetonato) via direct metalation starting from the corresponding triazolium iodides and palladium(ii) acetylacetonate is described herein. All complexes were characterized by 1H- and 13C-NMR spectroscopy and high resolution mass spectrometry. Additionally, two of the complexes were characterized by single crystal X-ray crystallography confirming a square-planar coordination geometry of the palladium(ii) center. A delocalized bonding situation was observed within the triazolylidene rings as well as for the acac ligand respectively. Complex 2 was found to be an efficient pre-catalyst for the Suzuki-Miyaura cross coupling reaction between aryl-bromides or -chlorides with phenylboronic acid.
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Keywords:
mesoionic carbenes; triazolylidenes; palladium; Suzuki-Miyaura cross coupling; click chemistry; abnormal carbenes
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MDPI and ACS Style
Hettmanczyk, L.; Schmid, B.; Hohloch, S.; Sarkar, B. Palladium(ii)-Acetylacetonato Complexes with Mesoionic Carbenes: Synthesis, Structures and Their Application in the Suzuki-Miyaura Cross Coupling Reaction. Molecules 2016, 21, 1561.
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