198345-82-3Relevant articles and documents
Sequential Organozinc Formation and Negishi Cross-Coupling of Amides Catalysed by Cobalt Salt
Dorval, Céline,Dubois, Elodie,Bourne-Branchu, Yann,Gosmini, Corinne,Danoun, Grégory
supporting information, p. 1777 - 1780 (2019/02/26)
Herein, a cobalt-catalysed Negishi-type cross-coupling of amide derivatives is described. Apart from being the first example of cobalt-catalysed Negishi-type coupling of amides, the process described employs a unique, simple, and cheap catalytic system to perform both the organozinc formation and the Negishi-type coupling. Indeed, the same cobalt(II) bromide salt used to form the arylzinc species from aryl bromides is then re-used to perform the cross coupling of this resulting arylzinc with N-benzoyl glutarimides at room temperature. The main advantages of the reaction presented are its robustness and ease of use. Indeed, the reactions of organozinc formation and Negishi-type coupling are performed without precautions toward water or oxygen. (Figure presented.).
Electron-deficient olefin ligands enable generation of quaternary carbons by Ni-catalyzed cross-coupling
Huang, Chung-Yang,Doyle, Abigail G.
supporting information, p. 5638 - 5641 (2015/05/20)
A Ni-catalyzed Negishi cross-coupling with 1,1-disubstituted styrenyl aziridines has been developed. This method delivers valuable β-substituted phenethylamines via a challenging reductive elimination that affords a quaternary carbon. A novel electron-deficient olefin ligand, Fro-DO, proved crucial for achieving high rates and chemoselectivity for C-C bond formation over β-H elimination. This ligand is easy to access, is stable, and presents a modular framework for reaction discovery and optimization. We expect that these attributes, combined with the fact that the ligands impart distinct electronic properties to a metal, will support the invention of new transformations not previously possible using established ligands.
Nickel-catalyzed enantioselective arylation of pyridinium ions: Harnessing an iminium ion activation mode
Chau, Stephen T.,Lutz, J. Patrick,Wu, Kevin,Doyle, Abigail G.
supporting information, p. 9153 - 9156 (2013/09/12)
A nickel for your thoughts.?? An enantioselective nickel-catalyzed cross-coupling between N-acylpyridinium salts and organozinc reagents is reported. The catalytic system, which is comprised of an air-stable NiII source and a chiral phosphoramidite ligand, affords 2-substituted-2,3-dihydro-4-pyridones with up to >99 % ee. Copyright
