Synthesis of symmetrical and unsymmetrical N,N'-diaryl guanidines via copper/N-methylglycine-catalyzed arylation of guanidine nitrate.
CuI/N-methylglycine-catalyzed coupling reaction of guanidine nitrate with both aryl iodides and bromides takes place at 70-100 °C, affording symmetrical N,N'-diaryl guanidines with good to excellent yields. Unsymmetrical N,N'-diaryl guanidines can be assembled via monoarylation of guanidine nitrate with aryl iodides bearing a strong electron-withdrawing group and subsequent coupling with another aryl iodide.
State Key Laboratory of Natural Medicines, Center of Drug Discovery, China Pharmaceutical University, Nanjing 210009, China.
Hui
H
Xing
Ye
Y
Zhang
Yisheng
Y
Lai
Yongwen
Y
Jiang
Dawei
D
Ma
D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D019791:Guanidine / Q000138:chemical synthesis* / Q000737:chemistry*; D006146:Guanidines / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D012521:Sarcosine / Q000737:chemistry*; D013237:Stereoisomerism
D006146:Guanidines; D003300:Copper; D019791:Guanidine; D012521:Sarcosine