5818-05-3Relevant academic research and scientific papers
Ligand-accelerated iron- and cobalt-catalyzed cross-coupling reactions between N-heteroaryl halides and aryl magnesium reagents
Kuzmina, Olesya M.,Steib, Andreas K.,Markiewicz, John T.,Flubacher, Dietmar,Knochel, Paul
, (2013)
Quinoline and isoquinoline dramatically increase the rate and yield of Fe- and Co-catalyzed cross-coupling reactions. This new catalytic process extends the scope of such cross-coupling reactions to include complex functional groups and allows heteroaryl-
NiH-Catalyzed Hydroamination/Cyclization Cascade: Rapid Access to Quinolines
Chen, Qian,Gao, Yang,Hu, Xiao-Qiang,Huo, Yanping,Li, Xianwei,Yang, Simin
, p. 7772 - 7779 (2021/06/30)
Despite the significant success of metal-H-catalyzed hydroamination methodologies, considerable limitations still exist in the selective hydroamination of alkynes, especially for terminal alkynes. Herein, we develop a highly efficient NiH catalytic system that activates readily available alkynes for a cascade hydroamination/cyclization reaction with anthranils. This mild, operationally simple protocol is amenable to a wide array of alkynes including terminal and internal, aryl and alkyl, electron-deficient and electron-rich ones, delivering structurally diverse quinolines in useful to excellent yields (>80 examples, up to 93% yield). The utility of this procedure is exhibited in the late-stage functionalization of several natural products and in the concise synthesis of an antitumor molecule graveolinine and a triplex DNA intercalator. Preliminary mechanistic experiments suggest an alkenylnickel-mediated alkyne hydroamination and an intramolecular cyclization/aromatization of putative enamine intermediates.
Practical iron- and cobalt-catalyzed cross-coupling reactions between n-heterocyclic halides and aryl or heteroaryl magnesium reagents
Kuzmina, Olesya M.,Steib, Andreas K.,Fernandez, Sarah,Boudot, Willy,Markiewicz, John T.,Knochel, Paul
supporting information, p. 8242 - 8249 (2015/05/27)
The reaction scope of iron- and cobalt-catalyzed cross-coupling reactions in the presence of isoquinoline (quinoline) in the solvent mixture tBuOMe/THF has been further investigated. Various 2-halogenated pyridine, pyrimidine, and triazine derivatives were arylated under these mild conditions in excellent yields. The presence of isoquinoline allows us to perform Fe-catalyzed cross-coupling reactions between 6-chloroquinoline and aryl magnesium reagents. Furthermore, it was found that the use of 10% N,N-dimethylquinoline-8-amine increases the yields of some Co-catalyzed cross-coupling reactions with chloropyridines bearing electron-withdrawing substituents. Iron out your coupling! The use of iron and cobalt catalysts in a combination with only 10% isoquinoline represents a practical method for the cross-coupling reactions of various 2-halogenopyridines, -pyrimidines, and -triazines, as well as 6-halogenoquinolines with functionalized aryl or heteroaryl Grignard reagents (see scheme).
