Palladium-catalyzed C-N and C-O bond formation of N-substituted 4-bromo-7-azaindoles with amides, amines, amino acid esters and phenols

Simple and efficient procedures for palladium-catalyzed cross-coupling reactions of N-substituted 4-bromo-7-azaindole (1H-pyrrole[2,3-b]pyridine), with amides, amines, amino acid esters and phenols through C-N and C-O bond formation have been developed. The C-N cross-coupling reaction of amides, ami...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2012-11, Vol.8 (1), p.2004-2018
Main Authors: Surasani, Rajendra, Kalita, Dipak, Rao, A V Dhanunjaya, Chandrasekhar, K B
Format: Article
Language:English
Subjects:
7-azaindole
Chemistry
C–N bond
C–O bond
Full Research Paper
ligand
palladium catalyst
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Summary:Simple and efficient procedures for palladium-catalyzed cross-coupling reactions of N-substituted 4-bromo-7-azaindole (1H-pyrrole[2,3-b]pyridine), with amides, amines, amino acid esters and phenols through C-N and C-O bond formation have been developed. The C-N cross-coupling reaction of amides, amines and amino acid esters takes place rapidly by using the combination of Xantphos, Cs(2)CO(3), dioxane and palladium catalyst precursors Pd(OAc)(2)/Pd(2)(dba)(3). The combination of Pd(OAc)(2), Xantphos, K(2)CO(3) and dioxane was found to be crucial for the C-O cross-coupling reaction. This is the first report on coupling of amides, amino acid esters and phenols with N-protected 4-bromo-7-azaindole derivatives.
ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.8.227