Assisted Tandem Palladium(II)/Palladium(0)-Catalyzed C- and N-Arylations of Quinoxalin-2(1H)-ones in Water

被引:77
作者
Carrer, Amandine [1 ]
Brion, Jean-Daniel [1 ]
Alami, Mouad [1 ]
Messaoudi, Samir [1 ]
机构
[1] Univ Paris 11, CNRS, BioCIS UMR 8076, LabEx LERMIT,Fac Pharm,Lab Chim Therapeut,Equipe, F-92296 Chatenay Malabry, France
关键词
assisted tandem catalysis; C-arylation; N-arylation; palladium catalysis; quinoxalinones; MULTIFUNCTIONAL PALLADIUM CATALYSIS; ZEROVALENT PALLADIUM; CLOSING METATHESIS; OLEFIN METATHESIS; COMPLEXES; TRANSFORMATIONS; PD(OAC)(2); REACTIVITY; CHEMISTRY; SEQUENCE;
D O I
10.1002/adsc.201400662
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A straightforward assisted tandem palladium(II)- and palladium(0)-catalyzed direct C-3 and N-4 arylation of quinoxalin-2(1H)-ones with boronic acids and aryl halides in water as safe and cheap solvent is reported. This environmentally friendly catalytic protocol is compatible with a wide range of functional groups and allows construction of various biologically important quinoxalin-2(1H)-one backbones.
引用
收藏
页码:3821 / 3830
页数:10
相关论文
共 35 条
[1]   Two birds with one metallic stone: Single-pot catalysis of fundamentally different transformations [J].
Ajamian, A ;
Gleason, JL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (29) :3754-3760
[2]  
Ajamian A., 2004, Angew. Chem, V116, P3842
[3]   EVIDENCE OF THE FORMATION OF ZEROVALENT PALLADIUM FROM PD(OAC)2 AND TRIPHENYLPHOSPHINE [J].
AMATORE, C ;
JUTAND, A ;
MBARKI, MA .
ORGANOMETALLICS, 1992, 11 (09) :3009-3013
[4]   RATES AND MECHANISM OF THE FORMATION OF ZEROVALENT PALLADIUM COMPLEXES FROM MIXTURES OF PD(OAC)(2) AND TERTIARY PHOSPHINES AND THEIR REACTIVITY IN OXIDATIVE ADDITIONS [J].
AMATORE, C ;
CARRE, E ;
JUTAND, A ;
MBARKI, MA .
ORGANOMETALLICS, 1995, 14 (04) :1818-1826
[5]   Mechanistic and kinetic studies of palladium catalytic systems [J].
Amatore, C ;
Jutand, A .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) :254-278
[6]   Neutral palladium(0) complexes from Pd(OAc)2 and tri-2-furylphosphine and their reactivity in oxidative addition of iodobenzene [J].
Amatore, Christian ;
Jutand, Anny ;
Khalil, Fouad .
ARKIVOC, 2006, :38-48
[7]   One-pot multi-step synthesis: a challenge spawning innovation [J].
Broadwater, SJ ;
Roth, SL ;
Price, KE ;
Kobaslija, M ;
McQuade, DT .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (16) :2899-2906
[8]   Synthesis of 3,4-Disubstituted Quinolin-2-(1H)-ones via Palladium-Catalyzed Decarboxylative Arylation Reactions [J].
Carrer, Amandine ;
Brion, Jean-Daniel ;
Messaoudi, Samir ;
Alami, Mouad .
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (10) :2044-2054
[9]   Palladium(II)-Catalyzed Oxidative Arylation of Quinoxalin-2(1H)-ones with Arylboronic Acids [J].
Carrer, Amandine ;
Brion, Jean-Daniel ;
Messaoudi, Samir ;
Alami, Mouad .
ORGANIC LETTERS, 2013, 15 (21) :5606-5609
[10]   Chemistry, biological properties and SAR analysis of quinoxalinones [J].
Carta, A. ;
Piras, S. ;
Loriga, G. ;
Paglietti, G. .
MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2006, 6 (11) :1179-1200