Palladium-Catalyzed Coupling of N-Amino­azoles with 3-Halo-Substituted ­Quinolin-2(1H)-ones, Coumarins, Quin­oxalin-2(1H)-ones, and Chromenes

Thi Thanh Huyen Luong; Etienne Brachet; Jean Daniel Brion; Samir Messaoudi; Mouâd Alami

doi:10.1002/ejoc.201403501

Palladium-Catalyzed Coupling of N-Aminoazoles with 3-Halo-Substituted Quinolin-2(1H)-ones, Coumarins, Quinoxalin-2(1H)-ones, and Chromenes

Thi Thanh Huyen Luong
, Etienne Brachet
, Jean Daniel Brion
, Samir Messaoudi
, Mouâd Alami

Université Paris-Saclay

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

Abstract

An efficient and general palladium-catalyzed coupling of 3-bromoquinolin-2(1H)-ones, 3-bromocoumarins, 3-chloroquinoxalin-2(1H)-ones, and 3-iodo-2H-chromenes with a variety of 1-aminoazoles is described. The reaction proceeds cleanly in the presence of the Pd(OAc)₂/4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) catalytic system to provide the coupling products in good to excellent yields.

Original language	English
Pages (from-to)	1771-1780
Number of pages	10
Journal	European Journal of Organic Chemistry
Volume	2015
Issue number	8
DOIs	https://doi.org/10.1002/ejoc.201403501
Publication status	Published - 1 Mar 2015
Externally published	Yes

Keywords

Cross-coupling
Heterocycles
P ligands
Palladium
Synthetic methods

Access to Document

10.1002/ejoc.201403501

Cite this

@article{dd087181c83f4d58bc1930235e1dfdc5,

title = "Palladium-Catalyzed Coupling of N-Aminoazoles with 3-Halo-Substituted Quinolin-2(1H)-ones, Coumarins, Quinoxalin-2(1H)-ones, and Chromenes",

abstract = "An efficient and general palladium-catalyzed coupling of 3-bromoquinolin-2(1H)-ones, 3-bromocoumarins, 3-chloroquinoxalin-2(1H)-ones, and 3-iodo-2H-chromenes with a variety of 1-aminoazoles is described. The reaction proceeds cleanly in the presence of the Pd(OAc)2/4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) catalytic system to provide the coupling products in good to excellent yields.",

keywords = "Cross-coupling, Heterocycles, P ligands, Palladium, Synthetic methods",

author = "Luong, \{Thi Thanh Huyen\} and Etienne Brachet and Brion, \{Jean Daniel\} and Samir Messaoudi and Mou{\^a}d Alami",

note = "Publisher Copyright: {\textcopyright} 2015 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2015",

month = mar,

day = "1",

doi = "10.1002/ejoc.201403501",

language = "English",

volume = "2015",

pages = "1771--1780",

journal = "European Journal of Organic Chemistry",

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Palladium-Catalyzed Coupling of N-Aminoazoles with 3-Halo-Substituted Quinolin-2(1H)-ones, Coumarins, Quinoxalin-2(1H)-ones, and Chromenes. / Luong, Thi Thanh Huyen; Brachet, Etienne; Brion, Jean Daniel et al.
In: European Journal of Organic Chemistry, Vol. 2015, No. 8, 01.03.2015, p. 1771-1780.

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

TY - JOUR

T1 - Palladium-Catalyzed Coupling of N-Aminoazoles with 3-Halo-Substituted Quinolin-2(1H)-ones, Coumarins, Quinoxalin-2(1H)-ones, and Chromenes

AU - Luong, Thi Thanh Huyen

AU - Brachet, Etienne

AU - Brion, Jean Daniel

AU - Messaoudi, Samir

AU - Alami, Mouâd

PY - 2015/3/1

Y1 - 2015/3/1

N2 - An efficient and general palladium-catalyzed coupling of 3-bromoquinolin-2(1H)-ones, 3-bromocoumarins, 3-chloroquinoxalin-2(1H)-ones, and 3-iodo-2H-chromenes with a variety of 1-aminoazoles is described. The reaction proceeds cleanly in the presence of the Pd(OAc)2/4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) catalytic system to provide the coupling products in good to excellent yields.

AB - An efficient and general palladium-catalyzed coupling of 3-bromoquinolin-2(1H)-ones, 3-bromocoumarins, 3-chloroquinoxalin-2(1H)-ones, and 3-iodo-2H-chromenes with a variety of 1-aminoazoles is described. The reaction proceeds cleanly in the presence of the Pd(OAc)2/4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) catalytic system to provide the coupling products in good to excellent yields.

KW - Cross-coupling

KW - Heterocycles

KW - P ligands

KW - Palladium

KW - Synthetic methods

U2 - 10.1002/ejoc.201403501

DO - 10.1002/ejoc.201403501

M3 - Article

AN - SCOPUS:85027939663

SN - 1434-193X

VL - 2015

SP - 1771

EP - 1780

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 8