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  • 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.

The Journal of organic chemistry (2017-07-07)
Eric C Hansen, Changfeng Li, Sihang Yang, Dylan Pedro, Daniel J Weix
ABSTRACT

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).

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
(2Z,6Z)-N′2,N′6-Dicyanopyridine-2,6-bis(carboximidamide)
Pricing and availability is not currently available.
Sigma-Aldrich
4-Methoxypicolinimidamide hydrochloride, ≥95%
Pricing and availability is not currently available.
Sigma-Aldrich
Pyridine-2,6-bis(carboximidamide) dihydrochloride, ≥95%
Pricing and availability is not currently available.