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. 2025 May 13;81(Pt 6):492-496.
doi: 10.1107/S2056989025004025. eCollection 2025 Jun 1.

Phenyl palladium(II) iodide complexes isolated after Sonogashira coupling of iodo-benzenes with terminal alkynes

Eric Bosch  1
Affiliations

Phenyl palladium(II) iodide complexes isolated after Sonogashira coupling of iodo-benzenes with terminal alkynes

Eric Bosch. Acta Crystallogr E Crystallogr Commun. .

Abstract

The structures of four palladium complexes serendipitously isolated after palladium-catalyzed Sonogashira coupling of aryl iodides with terminal alkynes are reported, namely [3,5-bis-(tri-fluoro-meth-yl)phen-yl]iodido-bis-(tri-phenyl-phosphane)palladium(II), [Pd(C8H3F6)I(C18H15P)2], 1, (3,5-di-nitro-phen-yl)iodido-bis-(tri-phenyl-phosphane)palladium(II) ethyl acetate monosolvate, [Pd(C6H3N2O4)I(C18H15P)2]·C4H8O2, 2, (2,3,4-di-fluoro-phen-yl)iodido-bis-(tri-phen-yl-phosphane)palladium(II), [Pd(C6H2F3)I(C18H15P)2], 3, and (2,4,6-di-fluoro-phen-yl)iodido-bis-(tri-phenyl-phosphane)palladium(II) di-chloro-methane disolvate, [Pd(C6H2F3)I(C18H15P)2]·2CH2Cl2, 4. These complexes were isolated as red/orange crystals that co-eluted with the organic products of each reaction during flash chromatography. These complexes are oxidative addition products ArPdI(PPh3)2 where Ar = 3,5-bis-(tri-fluoro-meth-yl)phenyl, 3,5-di-nitro-phenyl, 2,3,4-tri-fluoro-phenyl and 2,4,6-tri-fluoro-3,5-di-iodo-phenyl. The isolation of these complexes provides some insight into the possible fate of the palladium catalyst.

Keywords: aryl palladium iodide; crystal structure; oxidative addition.

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Figures

Figure 1
Figure 1
Reaction equation for Sonogashira coupling.
Figure 2
Figure 2
Asymmetric unit of each of the oxidative addition products 1–4 with displacement ellipsoids drawn at the 50% level. An ethyl acetate solvent mol­ecule is included in the ASU of 2 and two di­chloro­methane solvent mol­ecules, one disordered, are included in structure 4. The major position of the disordered di­chloro­methane mol­ecule is shown.
Figure 3
Figure 3
(a) View of the crystal packing in structure 1 viewed along the a axis. (b) Plot of the Hirshfeld surface of 1 within the crystal structure with close contacts labelled x, y and z (see text).
See this image and copyright information in PMC

References

    1. Barbour, L. J. (2020). J. Appl. Cryst.53, 1141–1146.
    1. Bourhis, L. J., Dolomanov, O. V., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2015). Acta Cryst. A71, 59–75. - PMC - PubMed
    1. Bruno, I. J., Cole, J. C., Edgington, P. R., Kessler, M., Macrae, C. F., McCabe, P., Pearson, J. & Taylor, R. (2002). Acta Cryst. B58, 389–397. - PubMed
    1. Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst.42, 339–341.
    1. Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. - PMC - PubMed

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