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

Mohr, Yorck and Hisler, Gaelle and Grousset, Leone and Roux, Yoann and Quadrelli, Elsje Alessandra and Wisser, Florian M. and Canivet, Jerome (2020) Nickel-catalyzed and Li-mediated regiospecific C-H arylation of benzothiophenes. GREEN CHEMISTRY, 22 (10). pp. 3155-3161. ISSN 1463-9262, 1463-9270

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Abstract

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.

Item Type: Article
Uncontrolled Keywords: EFFICIENT SYNTHESIS; FUNCTIONALIZATION; HETEROARENES; RALOXIFENE; ACCESS; PD; DERIVATIVES; THIOPHENE; COUPLINGS; INDOLES;
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Anorganische Chemie
Depositing User: Dr. Gernot Deinzer
Date Deposited: 23 Mar 2021 11:33
Last Modified: 23 Mar 2021 11:33
URI: https://pred.uni-regensburg.de/id/eprint/44536

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