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Phenol Derivatives in Ruthenium-Catalyzed C-H Arylation: A General Synthetic Access to Azole-Based Congested Polyaromatics

Abstract : Aryl triflates and related phenolates are suitable electrophile coupling partners for the ruthenium-catalyzed direct arylation of heteroaromatic substrates using azole N-directed sp 2-C-H activation. We report herein convenient conditions in the efficient ortho-C-H functionalization of aryl-pyrazoles, thiazoles and pyridines where [RuCl2(p-Cym)]2 precatalyst is employed with pivalic acid (PivOH) as co-catalyst. Different phenolate derivatives were successfully coupled which tolerate a large scope of electron-rich substituents in para-, meta-and highly hindered ortho-position. Electron-withdrawing aryl triflates were found less reactive, making the general reactivity of these electrophiles complementary to those of aryl chlorides and deactivated bromides. This cost-effective ruthenium C-H activation/arylation synthesis of poly(hetero)aromatics was concurrently examined using triflates, mesylates, sulfonates and carbonates, and was also successfully extended to the use of diethyl carbonate as an eco-friendly solvent.
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https://hal.archives-ouvertes.fr/hal-03664152
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Soumis le : mardi 10 mai 2022 - 17:55:54
Dernière modification le : mercredi 11 mai 2022 - 03:48:56

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Julien Roger, Jean-Cyrille Hierso. Phenol Derivatives in Ruthenium-Catalyzed C-H Arylation: A General Synthetic Access to Azole-Based Congested Polyaromatics. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2018, 2018 (35), pp.4953-4958. ⟨10.1002/ejoc.201800312⟩. ⟨hal-03664152⟩

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