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