CuI/4-hydro-L-proline as a more effective catalytic system for coupling of aryl bromides with N-boc hydrazine and aqueous ammonia.
CuI/4-hydroxy-l-proline-catalyzed coupling of aryl bromides and N-Boc hydrazine takes place in DMSO at 80 degrees C to give N-aryl hydrazides. When aryl iodides are employed, this reaction completes at 50 degrees C and no ligand is required. Under the catalysis of CuI/4-hydroxy-l-proline, the coupling reaction of aqueous ammonia with aryl bromides proceeds smoothly at 50 degrees C to afford primary arylamines. In this case K(2)CO(3) is found as a better base than Cs(2)CO(3). These processes allow assembly of N-aryl hydrazides and primary arylamines that bear a wide range of functional groups including hydroxyl, amine, trifluoromethyl, ester, nitro, and ketone.
Jiang
Liqin
L
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
Lu
Xu
X
Zhang
Hui
H
Jiang
Yongwen
Y
Ma
Dawei
D
D000641:Ammonia / Q000737:chemistry*; D000814:Aniline Compounds / Q000138:chemical synthesis*; D001969:Bromobenzenes / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D006573:Heterocyclic Compounds, 1-Ring / Q000138:chemical synthesis*; D006834:Hydrazines / Q000737:chemistry*; D006909:Hydroxyproline / Q000737:chemistry*; D007454:Iodides / Q000737:chemistry
D000814:Aniline Compounds; D001969:Bromobenzenes; D006573:Heterocyclic Compounds, 1-Ring; D006834:Hydrazines; D007454:Iodides; D000641:Ammonia; D003300:Copper; D006909:Hydroxyproline