Suzuki-Miyaura Reactions Catalyzed by C2-Symmetric Pd-Multi-Dentate N-Heterocyclic Carbene Complexes

被引：13

作者：

Jiang, Lan ^{[1
,2
]}

Shan, Fengjun ^{[2
]}

Li, Zhengning ^{[2
]}

Zhao, Defeng ^{[1
]}

机构：

[1] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116024, Peoples R China

[2] Dalian Univ, Coll Environm & Chem Engn, Dalian 116622, Peoples R China

来源：

MOLECULES | 2012年 / 17卷 / 10期

关键词：

imidazolium salt; N-heterocyclic carbene; palladium; Suzuki-Miyaura coupling; catalysis; CROSS-COUPLING REACTIONS; ARYL CHLORIDES; PALLADIUM(II) COMPLEXES; HIGHLY EFFICIENT; ATOM-EFFICIENT; HECK; NHC; LIGANDS; BROMIDES; HALIDES;

D O I：

10.3390/molecules171012121

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Suzuki-Miyaura coupling reactions are promoted by Pd complexes ligated with C-2-symmetric multi-dentate N-heterocyclic carbenes derived in situ from Pd(OAc)(2) and imidazolium salts. Good to excellent yields were obtained for aryl bromides as substrates. Turnover numbers of up to 10(5) could be achieved with 5 x 10(-4) mol% of Pd(OAc)(2)/1 x 10(-3) mol% NHC precatalyst in 24 h.

引用

页码：12121 / 12139

页数：19

共 50 条

[11] Preparation and characterization of PEPPSI-palladium N-heterocyclic carbene complexes using benzimidazolium salts catalyzed Suzuki-Miyaura cross coupling reaction and their antitumor and antimicrobial activities
Boubakri, Lamia
Dridi, Khaireddine
Al-Ayed, Abdullah Sulaiman
Ozdemir, Ismail
Yasar, Sedat
Hamdi, Naceur
JOURNAL OF COORDINATION CHEMISTRY, 2019, 72 (03) : 516 - 527
[12] Monodentate Chiral N-Heterocyclic Carbene-Palladium-Catalyzed Asymmetric Suzuki-Miyaura and Kumada Coupling
Wu, Linglin
Salvador, Alvaro
Ou, Arnold
Shi, Ming Wen
Skelton, Brian W.
Dorta, Reto
SYNLETT, 2013, 24 (10) : 1215 - 1220
[13] N-Heterocyclic Carbene Conjugated with Poly(ethylene glycol) for Palladium-Catalyzed Suzuki-Miyaura Coupling in Aqueous Solvents
Shi, Ji-cheng
Yu, Hongwei
Jiang, Dahong
Yu, Mei
Huang, Yanxian
Nong, Lanping
Zhang, Qing
Jin, Zilin
CATALYSIS LETTERS, 2014, 144 (01) : 158 - 164
[14] Triazole-Functionalized N-Heterocyclic Carbene Complexes of Palladium and Platinum and Efficient Aqueous Suzuki-Miyaura Coupling Reaction
Gu, Shaojin
Xu, Hui
Zhang, Na
Chen, Wanzhi
CHEMISTRY-AN ASIAN JOURNAL, 2010, 5 (07) : 1677 - 1686
[15] Imidazol(in)ium carboxylates as N-heterocyclic carbene ligand precursors for Suzuki-Miyaura reactions
Tudose, Adriana
Delaude, Lionel
Andre, Benoit
Demonceau, Albert
TETRAHEDRON LETTERS, 2006, 47 (48) : 8529 - 8533
[16] Synthesis and catalytic applications of palladium N-heterocyclic carbene complexes as efficient pre-catalysts for Suzuki-Miyaura and Sonogashira coupling reactions
Boubakri, L.
Yasar, S.
Dorcet, V.
Roisnel, T.
Bruneau, C.
Hamdi, N.
Ozdemir, I.
NEW JOURNAL OF CHEMISTRY, 2017, 41 (12) : 5105 - 5113
[17] An Efficient Protocol for Palladium N-Heterocyclic Carbene-Catalysed Suzuki-Miyaura Reaction at room temperature
Akkoc, Mitat
Imik, Fatma
Yasar, Sedat
Dorcet, Vincent
Roisnel, Thiery
Bruneau, Christian
Ozdemir, Ismail
CHEMISTRYSELECT, 2017, 2 (20): : 5729 - 5734
[18] Palladium biphenyl N-heterocyclic carbene complexes: Synthesis, structure and their catalytic efficiency in water mediated Suzuki-Miyaura cross-coupling reaction
Seva, Lavudi
Hwang, Wen-Shu
Sabiah, Shahulhameed
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2016, 418 : 125 - 131
[19] Sterically hindered N-heterocyclic carbene/palladium(ii) catalyzed Suzuki-Miyaura coupling of nitrobenzenes
Chen, Kai
Chen, Wei
Yi, Xiaofei
Chen, Wanzhi
Liu, Miaochang
Wu, Huayue
CHEMICAL COMMUNICATIONS, 2019, 55 (63) : 9287 - 9290
[20] Phosphine/N-heterocyclic carbene palladium complex for Suzuki-Miyaura cross-coupling reactions: The role of water on activity
Lahneche, Youssra Doria
Lachguar, Abdelhak
Mouton, Clement
Daran, Jean-Claude
Manoury, Eric
Poli, Rinaldo
Benslimane, Meriem
Labande, Agnes
Deydier, Eric
INORGANICA CHIMICA ACTA, 2019, 492 : 91 - 97

← 1 2 3 4 5 →