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Copper-Catalysed Allylic Substitution Using 2,8,14,20-Tetrapentylresorcinarenyl-Substituted Imidazolium Salts

Abstract : Unsymmetrical imidazolium salts, each having one nitrogen atom (N1) substituted by a cavity-shaped TPR group (TPR = 2,8,14,20-tetrapentylresorcinaren-5-yl), were tested in situ as proligands for the copper-catalysed allylic arylation of cinnamyl bromide with arylmagnesium halides. The catalytic systems produced mixtures of linear (l) and branched (b) arylated compounds in variable proportions, with the b/l ratio being the highest (78:22) for the most crowded imidazolium salt used, namely that in which the second nitrogen atom (N2) was substituted by a mesityl group. An N-heterocyclic carbene complex obtained from one of the imidazolium salts was characterised by an X-ray diffraction study
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01259525
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Submitted on : Wednesday, January 20, 2016 - 3:27:28 PM
Last modification on : Wednesday, January 29, 2020 - 9:30:20 AM

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Murat Kaloğlu, Neslihan Şahin, David Semeril, Eric Brenner, Dominique Matt, et al.. Copper-Catalysed Allylic Substitution Using 2,8,14,20-Tetrapentylresorcinarenyl-Substituted Imidazolium Salts. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2015, 2015 (33), pp.7310--7316. ⟨10.1002/ejoc.201501070⟩. ⟨hal-01259525⟩

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