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.
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
Liqin
L
Jiang
Xu
X
Lu
Hui
H
Zhang
Yongwen
Y
Jiang
Dawei
D
Ma
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