380383-81-3Relevant articles and documents
CuI/4-hydro-L-proline as a more effective catalytic system for coupling of aryl bromides with N-boc hydrazine and aqueous ammonia
Jiang, Liqin,Lu, Xu,Zhang, Hui,Jiang, Yongwen,Ma, Dawei
experimental part, p. 4542 - 4546 (2009/09/25)
(Chemical Equation Presented) CuI/4-hydroxy-L-proline-catalyzed coupling of aryl bromides and N-Boc hydrazine takes place in DMSO at 80°C to give N-aryl hydrazides. When aryl iodides are employed, this reaction completes at 50°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°C to afford primary arylamines. In this case K 2CO3 is found as a better base than Cs2CO 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.
Synthesis of C-15 vindoline analogues by palladium-catalyzed cross-coupling reactions
Johnson, Peter D.,Sohn, Jeong-Hun,Rawal, Viresh H.
, p. 7899 - 7902 (2007/10/03)
(Chemical Equation Presented) Described are general protocols for the rapid construction of various C-15-substituted analogues of vindoline using palladium-catalyzed cross-coupling reactions. The required bromo-and iodovindolines were prepared in high yie
Synthesis of N-aryl hydrazides by copper-catalyzed coupling of hydrazides with aryl iodides.
Wolter,Klapars,Buchwald
, p. 3803 - 3805 (2007/10/03)
[reaction--see text] A convenient method for intermolecular N-arylation of hydrazides with substituted aryl iodides in the presence of a copper catalyst and Cs(2)CO(3) is reported. The C-N coupling of N-Boc hydrazine with para- and meta-substituted aryl iodides afforded the N-arylated products A, regioselectively. A reversal in regioselectivity is observed for the arylation of benzoic hydrazide with ortho-substituted aryl iodides, providing the N'-arylated products B.
