Nickel-catalyzed and Li-mediated regiospecific C-H arylation of benzothiophenes - Université Claude Bernard Lyon 1 Accéder directement au contenu
Article Dans Une Revue Green Chemistry Année : 2020

Nickel-catalyzed and Li-mediated regiospecific C-H arylation of benzothiophenes

Résumé

A nickel-based catalytic system for the regiospecific C2-H arylation of benzothiophene has been established. NiCl2(bpy) is used as catalyst in combination with LiHMDS as base in dioxane. The catalytic system is applicable to a variety of funtionalized benzothiophenes, as well as other heteroarenes including thiophene, benzodithiophene, benzofuran and selenophene in combination with iodo aryl electrophiles. The role of LiHMDS as uniquely potent base and a postulated mechanism are discussed. The applicability of this system is finally demonstrated for the synthesis of an intermediate of anactive pharmaceutical ingredient.
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Dates et versions

hal-02877066 , version 1 (31-07-2020)

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Y. Mohr, G. Hisler, L. Grousset, Y. Roux, F. Wisser, et al.. Nickel-catalyzed and Li-mediated regiospecific C-H arylation of benzothiophenes. Green Chemistry, 2020, 22 (10), pp.3155-3161. ⟨10.1039/d0gc00917b⟩. ⟨hal-02877066⟩
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