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Nickel-Catalyzed Amination of Aryl Chlorides and Sulfamates in 2-Methyl-THF.

ABSTRACT: 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.

SUBMITTER: Fine Nathel NF

PROVIDER: S-EPMC4165539 | biostudies-literature | 2014 Sep

REPOSITORIES: biostudies-literature

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Nickel-Catalyzed Amination of Aryl Chlorides and Sulfamates in 2-Methyl-THF.

Fine Nathel Noah F NF Kim Junyong J Hie Liana L Jiang Xingyu X Garg Neil K NK

ACS catalysis 20140820 9

The nickel-catalyzed amination of aryl <i>O</i>-sulfamates and chlorides using the green solvent 2-methyl-THF is reported. This methodology employs the commercially available and air-stable precatalyst NiCl<sub>2</sub>(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 descri ...[more]

PMID: 25243095

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