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 inJournal 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
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 19.06.2020
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALKYL-HALIDES
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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