Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Coupling of Challenging Heteroaryl Halides with Alkyl Halides via Nickel-Catalyzed Cross-Electrophile Coupling

Coupling of Challenging Heteroaryl Halides with Alkyl Halides via Nickel-Catalyzed Cross-Electrophile Coupling
Dylan Pedro, Daniel J. Weix, Sihang Yang, Eric C. Hansen, Changfeng Li
Despite their importance, the synthesis of alkylated heterocycles from the cross-coupling of Lewis basic nitrogen heteroaryl halides with alkyl halides remains a challenge. We report here a general solution to this challenge enabled by a new collection of ligands based around 2-pyridyl-N-cyanocarboxamidine and 2-pyridylcarboxamidine cores. Both primary and secondary alkyl halides can be coupled with 2-, 3-, and 4-pyridyl halides as well as other more complex heterocycles in generally good yields (41 examples, 69% ave yield).

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01334

DOI: 10.1021/acs.joc.7b01334

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