A general Pd/Cu-catalyzed C-H heteroarylation of 3-bromoquinolin-2(1H)-ones

Alexandre Bruneau; Jean Daniel Brion; Samir Messaoudi; Mouad Alami

doi:10.1039/c4ob01610f

A general Pd/Cu-catalyzed C-H heteroarylation of 3-bromoquinolin-2(1H)-ones

Alexandre Bruneau
, Jean Daniel Brion
, Samir Messaoudi
, Mouad Alami

Université Paris-Saclay

Research output: Contribution to journal › Article › peer-review

Abstract

3-(Heteroaryl)quinolin-2(1H)-ones were synthesized in good to excellent yields using a bimetallic catalytic system through the C-H heteroarylation strategy. Starting from 3-bromoquinolin-2(1H)-ones, various azoles have been successfully used. In all cases, the reactions take place rapidly in dioxane and efficiently proceed in the presence of a bimetallic Pd(OAc)₂/CuI as the catalyst, PPh₃ as the ligand and LiOtBu or KOAc as the base.

Original language	English
Pages (from-to)	8533-8541
Number of pages	9
Journal	Organic and Biomolecular Chemistry
Volume	12
Issue number	42
DOIs	https://doi.org/10.1039/c4ob01610f
Publication status	Published - 14 Nov 2014
Externally published	Yes

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title = "A general Pd/Cu-catalyzed C-H heteroarylation of 3-bromoquinolin-2(1H)-ones",

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AU - Bruneau, Alexandre

AU - Brion, Jean Daniel

AU - Messaoudi, Samir

AU - Alami, Mouad

N1 - Publisher Copyright: © the Partner Organisations 2014.

PY - 2014/11/14

Y1 - 2014/11/14

N2 - 3-(Heteroaryl)quinolin-2(1H)-ones were synthesized in good to excellent yields using a bimetallic catalytic system through the C-H heteroarylation strategy. Starting from 3-bromoquinolin-2(1H)-ones, various azoles have been successfully used. In all cases, the reactions take place rapidly in dioxane and efficiently proceed in the presence of a bimetallic Pd(OAc)2/CuI as the catalyst, PPh3 as the ligand and LiOtBu or KOAc as the base.

AB - 3-(Heteroaryl)quinolin-2(1H)-ones were synthesized in good to excellent yields using a bimetallic catalytic system through the C-H heteroarylation strategy. Starting from 3-bromoquinolin-2(1H)-ones, various azoles have been successfully used. In all cases, the reactions take place rapidly in dioxane and efficiently proceed in the presence of a bimetallic Pd(OAc)2/CuI as the catalyst, PPh3 as the ligand and LiOtBu or KOAc as the base.

U2 - 10.1039/c4ob01610f

DO - 10.1039/c4ob01610f

M3 - Article

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SN - 1477-0520

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JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 42

ER -

A general Pd/Cu-catalyzed C-H heteroarylation of 3-bromoquinolin-2(1H)-ones

Abstract

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