Nickel-catalyzed and Li-mediated regiospecific C–H arylation of benzothiophenes
2020
Mohr, Yorck | Hisler, Gaëlle | Grousset, Léonie | Roux, Yoann | Quadrelli, Elsje Alessandra | Wisser, Florian M. | Canivet, Jérôme
A nickel-based catalytic system for the regiospecific C2–H arylation of benzothiophene has been established. NiCl₂(bpy) is used as a catalyst in combination with LiHMDS as a base in dioxane. The catalytic system is applicable to a variety of functionalized benzothiophenes, as well as other heteroarenes including thiophene, benzodithiophene, benzofuran and selenophene in combination with iodo aryl electrophiles. The role of LiHMDS as a uniquely potent base and a postulated mechanism are discussed. The applicability of this system is finally demonstrated for the synthesis of an intermediate of an active pharmaceutical ingredient.
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