Ligandless Palladium-Catalyzed Regioselective Direct C-H Arylation of Imidazo[1,2-a]imidazole Derivatives. - Archive ouverte HAL
Article Dans Une Revue Journal of Organic Chemistry Année : 2015

Ligandless Palladium-Catalyzed Regioselective Direct C-H Arylation of Imidazo[1,2-a]imidazole Derivatives.

Résumé

Herein a novel access to functionalizable 6-substituted imidazo[1,2-a]imidazole scaffolds is described. The reactivity of this heterobicyclic unit toward direct C-H arylation was studied, and conditions allowing regioselective arylation at position 3 were successfully developed. The practicability of this method is manifested by the ligandless conditions and low catalyst loading. The strategy is functional group tolerant and provides rapid access to a large variety of 3,6-di(hetero)arylated imidazo[1,2-a]imidazole derivatives. A second arylation at position 2 was then carried out, and a library of diversified 2,3,6-tri(hetero)arylated imidazo[1,2-a]imidazoles was generated in good yields. A one-pot, two-step procedure was finally developed.

Domaines

Matériaux
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Dates et versions

hal-01204848 , version 1 (24-09-2015)

Identifiants

Citer

Sandrine Grosse, Christelle Pillard, Stéphane Massip, Mathieu Marchivie, Christian Jarry, et al.. Ligandless Palladium-Catalyzed Regioselective Direct C-H Arylation of Imidazo[1,2-a]imidazole Derivatives.. Journal of Organic Chemistry, 2015, 80 (17), pp.8539-8551. ⟨10.1021/acs.joc.5b00534⟩. ⟨hal-01204848⟩
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