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Issue 10, 2020
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Nickel-catalyzed and Li-mediated regiospecific C–H arylation of benzothiophenes

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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.

Graphical abstract: Nickel-catalyzed and Li-mediated regiospecific C–H arylation of benzothiophenes

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Supplementary files

Article information


Submitted
13 Mar 2020
Accepted
21 Apr 2020
First published
21 Apr 2020

Green Chem., 2020,22, 3155-3161
Article type
Paper

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

Y. Mohr, G. Hisler, L. Grousset, Y. Roux, E. A. Quadrelli, F. M. Wisser and J. Canivet, Green Chem., 2020, 22, 3155
DOI: 10.1039/D0GC00917B

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