CuI/Oxalic Diamide Catalyzed Coupling Reaction of (Hetero)Aryl Chlorides and Amines.
A class of oxalic diamides are found to be effective ligands for promoting CuI-catalyzed aryl amination with less reactive (hetero)aryl chlorides. The reaction proceeds at 120 °C with K3PO4 as the base in DMSO to afford a wide range of (hetero)aryl amines in good to excellent yields. The bis(N-aryl) substituted oxalamides are superior ligands to N-aryl-N'-alkyl substituted or bis(N-alkyl) substituted oxalamides. Both the electronic nature and the steric property of the aromatic rings in ligands are important for their efficiency.
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Lu, Shanghai 200032, China.
Wei
W
Zhou
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Lu, Shanghai 200032, China.
Mengyang
M
Fan
School of Physical Science and Technology, ShanghaiTech , 319 Yueyang Road, Shanghai 200031, China.
Junli
J
Yin
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Lu, Shanghai 200032, China.
Yongwen
Y
Jiang
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Lu, Shanghai 200032, China.|School of Physical Science and Technology, ShanghaiTech , 319 Yueyang Road, Shanghai 200031, China.
Dawei
D
Ma
D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D002713:Chlorine / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D003958:Diamide / Q000737:chemistry*; D007454:Iodides / Q000737:chemistry*; D019815:Oxalic Acid / Q000737:chemistry*
D000588:Amines; D007454:Iodides; D003958:Diamide; D002713:Chlorine; D003300:Copper; C073870:cuprous iodide; D019815:Oxalic Acid