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

Soumik Biswas, Bo Qu*, Jean-Nicolas Desrosiers*, Younggi Choi, Nizar Haddad, Nathan K. Yee, Jinghua J. Song and Chris H. Senanayake

*Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, Connecticut 06877, United States, Email: bo.quboehringer-ingelheim.com, nick.desrosierspfizer.com

S. Biswas, B. Qu, J.-N. Desrosiers, Y. Choi, N. Haddad, N. K. Yee, J. J. Song, C. H. Senanayake, J. Org. Chem., 2020, 85, 8214-8220.

DOI: 10.1021/acs.joc.0c00549

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Abstract

5-Cyanoimidazole was identified as an inexpensive ligand for nickel-catalyzed cross-electrophile couplings for the preparation of various alkylated arene products with good yields. Furthermore, the scope of reductive couplings could be expanded to challenging substrates, such as sterically hindered neopentyl halides.

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Key Words

alkylated arenes, zinc

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ID: J42-Y2020