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Direct Amination of Azoles via Catalytic C−H, N−H Coupling
Organic Letters · 2009 · Vol. 11(7) · pp. 1607–1610
Daiki Monguchi✉(Kobe University)Taiki Fujiwara(Kobe University)Hirotoshi Furukawa(Kobe University)Atsunori Mori(Kobe University)
Abstract
C-H, N-H Coupling of azoles takes place with several amines in the presence of a copper catalyst to undergo amination at the 2-position. The reaction of benzothiazole with N-methylaniline in the presence of sodium acetate and 20 mol % Cu(OAc)(2) in xylene under an oxygen atmosphere afforded the aminated product in 81% yield.
Catalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsCatalytic Cross-Coupling ReactionsAminationChemistryCatalysisBenzothiazoleYield (engineering)CopperMedicinal chemistryOrganic chemistryCombinatorial chemistry
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References
Copper-Catalyzed Coupling of Alkylamines and Aryl Iodides: An Efficient System Even in an Air Atmosphere
Organic Letters · 2002 · 503 citations
Transition-Metal-Catalyzed Carbon-Carbon Bond Formation via Carbon-Hydrogen Bond Cleavage
Synthesis · 2008 · 778 citations
Evolution of a Fourth Generation Catalyst for the Amination and Thioetherification of Aryl Halides
Accounts of Chemical Research · 2008 · 1,855 citations
Palladium-Catalyzed Arylation of Azole Compounds with Aryl Halides in the Presence of Alkali Metal Carbonates and the Use of Copper Iodide in the Reaction
Bulletin of the Chemical Society of Japan · 1998 · 465 citations
C−C Bond Formation via Double C−H Functionalization: Aerobic Oxidative Coupling as a Method for Synthesizing Heterocoupled Biaryls
Organic Letters · 2007 · 474 citations
Rational Development of Practical Catalysts for Aromatic Carbon−Nitrogen Bond Formation
Accounts of Chemical Research · 1998 · 1,763 citations
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