Synthesis and X-ray diffraction study of thiosemicarbazone palladacycles with dppm

Marcos Rúa-Sueiro; Paula Munin-Cruz; Francisco Reigosa; José M. Vila; Juan M. Ortigueira

doi:10.3390/IOCC_2020-07352

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Synthesis and X-ray diffraction study of thiosemicarbazone palladacycles with dppm

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¹ Department of Inorganic Chemistry, Faculty of Chemistry, University of Santiago de Compostela, Santiago de Compostela

Published: 06 November 2020 by MDPI in The 2nd International Online Conference on Crystals session Crystal Engineering

https://doi.org/10.3390/IOCC_2020-07352

Abstract:

Cyclometallated compounds have been extensively studied, in particular those with palladium and platinum. This is because of their possible applications in medicinal chemistry, as anticancer or antimicrobial agents; in some cases with similar results as cisplatin, carboplatin or oxaliplatin. Also remarkable is their use as homogeneous catalysts, for example, in cross coupling reactions such as Suzuki-Miyaura or Mizoroki-Heck.

Herein we report the synthesis of different thiosemicarbazone ligands, which will be reacted with a palladium or platinum salt, to give the corresponding cyclometallated compounds; their reactivity with bis(diphenylphosphino)methane (dppm) will be studied.

Characterization has been carried by elemental analysis, IR spectroscopy, ¹H and ³¹P NMR spectroscopy. Also, 1c has been studied by X-ray diffraction.

Keywords: cyclometallation, thiosemicarbazone, palladium, platinum, X-ray diffraction

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Comments on this paper

Ulli Englert

13 November 2020

cyclometallation

I have read your contribution with interest. May I have a chemical question? Does cyclomettalation according to Scheme 2 formally procede with a release of HCl? Do you use an excess of the thiosemicarbazone as a base?
Happy weekend,

Ulli

Marcos Rúa Sueiro

20 November 2020

Hi,
Indeed, HCl is formally formed in cyclometallation (H+ and Cl- in ethanolic aqueous solution) but in this case is not needed base addition. In other reactions, e. g. with Schiff bases or iminophosphorane ligands, base addition like NaOAc or Na2CO3 is required in order to obtain the cyclometallated product.

Catherine Raptopoulou

14 November 2020

Comment

Nice work. I would like to ask the authors to provide better quality figures for the molecular and intermolecular crystal structures, if possible.