Nickel-Catalyzed Amination of Aryl Chlorides with Amides
A nickel-catalyzed amination of aryl chlorides with diverse amides via C-N bond cleavage has been realized under mild conditions. A broad substrate scope with excellent functional group tolerance at a low catalyst loading makes the protocol powerful for synthesizing various aromatic amines. The aryl chlorides could selectively couple to the amino fragments rather than the carbonyl moieties of amides. Our protocol complements the conventional amination of aryl chlorides and expands the usage of inactive amides.
Li, Jinpeng,Huang, Changyu,Wen, Daheng,Zheng, Qingshu,Tu, Bo,Tu, Tao
supporting information
p. 687 - 691
(2021/01/09)
Nickel-catalyzed amination of aryl chlorides and sulfamates in 2-methyl-THF
The nickel-catalyzed amination of aryl O-sulfamates and chlorides using the green solvent 2-methyl-THF is reported. This methodology employs the commercially available and air-stable precatalyst NiCl2(DME), is broad in scope, and provides access to aryl amines in synthetically useful yields. The utility of this methodology is underscored by examples of gram-scale couplings conducted with catalyst loadings as low as 1 mol % nickel. Moreover, the nickel-catalyzed amination described is tolerant of heterocycles and should prove useful in the synthesis of pharmaceutical candidates and other heteroatom-containing compounds.
Fine Nathel, Noah F.,Kim, Junyong,Hie, Liana,Jiang, Xingyu,Garg, Neil K.
p. 3289 - 3293
(2015/02/19)
Nickel-catalyzed coupling of fluoroarenes and amines
The combination of bis(cyclooctadiene)nickel [Ni(COD)2] and 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene hydrochloride (IPr×HCl) effectively catalyzes coupling of fluoroarenes with amines in the presence of sodium tert-butoxide (t-BuONa). A
Zhu, Feng,Wang, Zhong-Xia
p. 3694 - 3702
(2014/01/06)
AMINATION OF ARYL ALCOHOL DERIVATIVES
Embodiments of the invention provide methods and materials for chemical cross-coupling reactions that utilize aryl alcohol derivatives as cross-coupling partners. Embodiments of the invention include methods for the amination of aryl sulfamates and carbamates, which are attractive cross-coupling partners, particularly for use in multistep synthesis. Illustrative embodiments include versatile means to use simple derivatives of phenol as precursors to polysubstituted aryl amines, as exemplified by a concise synthesis of the antibacterial drug linezolid.
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Page/Page column 22-23; 27
(2012/07/27)
Nickel-catalyzed amination of aryl sulfamates and carbamates using an air-stable precatalyst
A facile nickel-catalyzed method to achieve the amination of synthetically useful aryl sulfamates and carbamates is reported. Contrary to most Ni-catalyzed amination reactions, this user-friendly approach relies on an air-stable Ni(II) precatalyst, which, when employed with a mild reducing agent, efficiently delivers aminated products in good to excellent yields. The scope of the method is broad with respect to both coupling partners and includes heterocyclic substrates.
Hie, Liana,Ramgren, Stephen D.,Mesganaw, Tehetena,Garg, Neil K.
supporting information; experimental part
p. 4182 - 4185
(2012/09/25)
Nickel-catalyzed amination of aryl sulfamates
Broad in scope: The first amination of aryl sulfamates, which are attractive cross-coupling partners, particularly for multistep syntheses, was achieved by using a nickel catalyst. The method provides a versatile means to use simple derivatives of phenol as precursors to polysubstituted aryl amines, as exemplified by a concise synthesis of the antibacterial drug linezolid (see scheme).
Ramgren, Stephen D.,Silberstein, Amanda L.,Yang, Yang,Garg, Neil K.
supporting information; experimental part
p. 2171 - 2173
(2011/04/25)
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