title: Nickel-Catalyzed Amination of Aryl Chlorides and Sulfamates in 2-Methyl-THF.
abstract: The nickel-catalyzed amination of arylO-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.
authors.affiliation: Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095, United States.
authors.forename: Noah F
authors.initials: NF
authors.lastname: Fine Nathel
authors.affiliation: Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095, United States.
authors.forename: Junyong
authors.initials: J
authors.lastname: Kim
authors.affiliation: Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095, United States.
authors.forename: Liana
authors.initials: L
authors.lastname: Hie
authors.affiliation: Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095, United States.
authors.forename: Xingyu
authors.initials: X
authors.lastname: Jiang
authors.affiliation: Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095, United States.
authors.forename: Neil K
authors.initials: NK
authors.lastname: Garg
keywords: 2-methyl-THF; amination; catalysis; cross-coupling; green chemistry; nickel