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Palladium-Catalysed Cross-Coupling Reactions Controlled by Noncovalent Zn···N Interactions

Abstract : Non-covalent interactions between halopyridine substrates and catalytically inert building blocks, namely zinc(II)-porphyrins and zinc(II)-salphens, influence the catalytic outcome of Suzuki-Miyaura and Mizoroki-Heck palladium-catalysed cross-coupling reactions. The weak Zn⋅⋅⋅N interactions between halopyridine substrates and zinc(II)-containing porphyrins and salphens, respectively, were studied by a combination of H NMR spectroscopy, UV/Vis studies, Job-Plot analysis and, in some cases, X-ray diffraction studies. Additionally, the former studies revealed unique supramolecular polymeric and dimeric rearrangements in the solid state featuring weak Br⋅⋅⋅N (halogen bonding), C-H⋅⋅⋅π, Br⋅⋅⋅π and π⋅⋅⋅π interactions. The reactivity of halopyridine substrates in homogeneous palladium-catalysed cross-coupling reactions was found to correlate with the binding strength between the zinc(II)-containing scaffolds and the corresponding halopyridine. Such observation is explained by the unfavourable formation of inactive over-coordinated halopyridine⋅⋅⋅palladium species. The presented approach is particularly appealing for those cases in which substrates and/or products deactivate (or partially poison) a transition-metal catalyst.
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Submitted on : Friday, May 19, 2017 - 4:19:29 PM
Last modification on : Thursday, March 5, 2020 - 2:07:09 PM
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Accepted manuscript online: 3 January 2017

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Mohamed Kadri, Jingran Hou, Vincent Dorcet, Thierry Roisnel, Lazhar Bechki, et al.. Palladium-Catalysed Cross-Coupling Reactions Controlled by Noncovalent Zn···N Interactions. Chemistry - A European Journal, Wiley-VCH Verlag, 2017, 23 (21), pp.5033-5043. ⟨10.1002/chem.201604780⟩. ⟨hal-01507248⟩

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