93971-09-6Relevant articles and documents
Metal-Reductant-Free Electrochemical Nickel-Catalyzed Couplings of Aryl and Alkyl Bromides in Acetonitrile
Perkins, Robert J.,Hughes, Alexander J.,Weix, Daniel J.,Hansen, Eric C.
supporting information, p. 1746 - 1751 (2019/08/20)
While reductive cross-electrochemical coupling is an attractive approach for the synthesis of complex molecules at both small and large scale, two barriers for large-scale applications have remained: the use of stoichiometric metal reductants and a need for amide solvents. In this communication, new conditions that address these challenges are reported. The nickel-catalyzed reductive cross-coupling of aryl bromides with alkyl bromides can be conducted in a divided electrochemical cell using acetonitrile as the solvent and diisopropylamine as the sacrificial reductant to afford coupling products in synthetically useful yields (22-80%). Additionally, the use of a combination of the ligands 4,4′,4″-tri-tert-butyl-2,2′:6′,2′-terpyridine and 4,4′-di-tert-butyl-2,2′-bipyridine is essential to achieve high yields.
Coupling of Challenging Heteroaryl Halides with Alkyl Halides via Nickel-Catalyzed Cross-Electrophile Coupling
Hansen, Eric C.,Li, Changfeng,Yang, Sihang,Pedro, Dylan,Weix, Daniel J.
, p. 7085 - 7092 (2017/07/26)
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).
REACTION OF DIALKYLPYRIDINES WITH STYRENE AND MASS-SPECTROMETRIC BEHAVIOR OF THE REACTION PRODUCTS
Tokmurzin, K.Kh.,Turgarina, R.,Zhumagaliev, S.Zh.
, p. 1133 - 1135 (2007/10/02)
The reaction of 2,4-dimethylpyridine with styrene gives 2-(3'-phenyl-propyl)-4-methyl- and 2-methyl-4-(3'-phenylpropyl)pyridine, but in the case of 2-methyl-5-ethylpyridine, the reaction gives only 2-(3'-phenylpropyl)-5-ethylpyridine.The mass spectra of the compounds obtained have been studied.
