Synthesis of N-aryl hydrazides by copper-catalyzed coupling of hydrazides with aryl iodides

Authors
Wolter, M Klapars, A Buchwald, SL
Citation
M. Wolter et al., Synthesis of N-aryl hydrazides by copper-catalyzed coupling of hydrazides with aryl iodides, ORG LETT, 3(23), 2001, pp. 3803-3805
Citations number
24
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
23
Year of publication
2001
Pages
3803 - 3805
Database
ISI
SICI code
1523-7060(20011115)3:23<3803:SONHBC>2.0.ZU;2-K
Abstract
[GRAPHICS] A convenient method for intermolecular N-arylation of hydrazides with subst ituted aryl iodides in the presence of a copper catalyst and Cs2CO3 is repo rted. The C-N coupling of N-Boc hydrazine with para- and meta-substituted a ryl iodides afforded the N-arylated products A, regioselectively. A reversa l in regioselectivity is observed for the arylation of benzoic hydrazide wi th ortho-substituted aryl iodides, providing the N'-arylated products B.