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

Eric C. Hansen | Zendy; Changfeng Li | Zendy; Sihang Yang | Zendy; Dylan J. Pedro | Zendy; Daniel J. Weix | Zendy

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

Author(s) -

Eric C. Hansen,

Changfeng Li,

Sihang Yang,

Dylan J. Pedro,

Daniel J. Weix

Publication year - 2017

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.7b01334

Subject(s) - halide , alkyl , alkylation , chemistry , electrophile , nickel , coupling (piping) , yield (engineering) , catalysis , medicinal chemistry , combinatorial chemistry , organic chemistry , materials science , metallurgy

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).

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