Synthesis of N-aryl hydrazides by copper-catalyzed coupling of hydrazides with aryl iodides.
[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.
Wolter
M
M
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Klapars
A
A
Buchwald
S L
SL
D001555:Benzene Derivatives / Q000737:chemistry*; D002384:Catalysis; D003300:Copper; D006834:Hydrazines / Q000138:chemical synthesis*; D006847:Hydrocarbons, Iodinated / Q000737:chemistry*; D007202:Indicators and Reagents
D001555:Benzene Derivatives; D006834:Hydrazines; D006847:Hydrocarbons, Iodinated; D007202:Indicators and Reagents; D003300:Copper