Nickel-Catalyzed Cross-Electrophile Reductive Couplings of Neopentyl Bromides with Aryl Bromides

5-Cyanoimidazole was identified as an inexpensive ligand for nickel-catalyzed cross-electrophile couplings by screening a diverse set of pharmaceutical compound library. A strategic screening approach led to the discovery of this novel ligand, which was successfully applied in the preparation of var...

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Bibliographic Details
Published in:Journal of organic chemistry Vol. 85; no. 12; pp. 8214 - 8220
Main Authors: Biswas, Soumik, Qu, Bo, Desrosiers, Jean-Nicolas, Choi, Younggi, Haddad, Nizar, Yee, Nathan K, Song, Jinghua J, Senanayake, Chris H
Format: Journal Article
Language:English
Published: United States 19-06-2020
Online Access:Get full text
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Summary:5-Cyanoimidazole was identified as an inexpensive ligand for nickel-catalyzed cross-electrophile couplings by screening a diverse set of pharmaceutical compound library. A strategic screening approach led to the discovery of this novel ligand, which was successfully applied in the preparation of various alkylated arene products with good to high yields. Furthermore, the properties of this ligand allowed expanding the scope of reductive couplings to challenging substrates, such as sterically hindered neopentyl halides, which are known to generate motifs that are prevalent in biologically active molecules.
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c00549