Monodentate Chiral N-Heterocyclic Carbene-Palladium-Catalyzed Asymmetric Suzuki-Miyaura and Kumada Coupling

被引：26

作者：

Wu, Linglin ^{[1
,2
]}

Salvador, Alvaro ^{[1
,2
]}

Ou, Arnold ^{[2
]}

Shi, Ming Wen ^{[2
]}

Skelton, Brian W. ^{[3
]}

Dorta, Reto ^{[1
,2
]}

机构：

[1] Univ Zurich, Inst Organ Chem, CH-8057 Zurich, Switzerland

[2] Univ Western Australia, Sch Chem & Biochem, Crawley, WA 6009, Australia

[3] Univ Western Australia, Ctr Microscopy Characterisat & Anal, Crawley, WA 6009, Australia

来源：

SYNLETT | 2013年 / 24卷 / 10期

关键词：

monodentate chiral NHC; palladium; asymmetric catalysis; Suzuki-Miyaura coupling; Kumada coupling; ENANTIOSELECTIVE SYNTHESIS; LIGANDS; COMPLEXES; BIARYLS; NICKEL; ARYLATION; BINOL;

D O I：

10.1055/s-0033-1338864

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Heterocyclic carbene ligands derived from C-2-symmetric diamine with naphthyl side chains are introduced as chiral monodentate ligands, and their palladium complexes (NHC)Pd(cin)Cl are prepared. These compounds exist as a mixture of diastereomers, and the palladium complexes can be successfully separated. When used in the asymmetric Suzuki-Miyaura and Kumada coupling, chiral biaryls can be obtained in high yield and moderate selectivity.

引用

页码：1215 / 1220

页数：6

共 50 条

[31] Synthesis and Application of N-Heterocyclic Carbene-Palladium Ligands with Glycerol Dendrons for the Suzuki-Miyaura Cross-Coupling in Water
Lukowiak, Maike C.
Meise, Markus
Haag, Rainer
SYNLETT, 2014, 25 (15) : 2161 - 2165
[32] N-Heterocyclic carbene-palladium(II)-1-methylimidazole complex-catalyzed Suzuki-Miyaura coupling of benzyl carbamates with arylboronic acids
Wang, Xiao-Xia
Luo, Mao-Jun
Lu, Jian-Mei
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (47) : 11438 - 11444
[33] N-heterocyclic carbene-palladium(II)-1-methylimidazole complex-catalyzed Suzuki-Miyaura coupling of benzyl sulfonates with arylboronic acids
Wang, Xiao-Xia
Xu, Bin-Bin
Song, Wen-Ting
Sun, Kai-Xin
Lu, Jian-Mei
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (17) : 4925 - 4930
[34] N-Heterocyclic Carbene-Palladium(II)-1-Methylimidazole Complex-Catalyzed Suzuki-Miyaura Coupling of Aryl Sulfonates with Arylboronic Acids
Wang, Zhan-Yong
Chen, Gao-Qi
Shao, Li-Xiong
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (15): : 6608 - 6614
[35] Efficient N-heterocyclic carbene palladium(II) catalysts for carbonylative Suzuki-Miyaura coupling reactions leading to aryl ketones and diketones
Ibrahim, Mansur
Malik, Imran
Mansour, Waseem
Sharif, Muhammad
Fettouhi, Mohammed
El Ali, Bassam
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2018, 859 : 44 - 51
[36] N-heterocyclic carbenes: III. N-heterocyclic carbene ligands based on abietane in Suzuki-Miyaura reaction
V. A. Glushkov
M. S. Valieva
O. A. Maiorova
E. V. Baigacheva
A. A. Gorbunov
Russian Journal of Organic Chemistry, 2011, 47 : 230 - 235
[37] N-Heterocyclic Carbenes: III. N-Heterocyclic Carbene Ligands Based on Abietane in Suzuki-Miyaura Reaction
Glushkov, V. A.
Valieva, M. S.
Maiorova, O. A.
Baigacheva, E. V.
Gorbunov, A. A.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 47 (02) : 230 - 235
[38] Amino acid-derived N-heterocyclic carbene palladium complexes for aqueous phase Suzuki-Miyaura couplings
Steeples, Elliot
Kelling, Alexandra
Schilde, Uwe
Esposito, Davide
NEW JOURNAL OF CHEMISTRY, 2016, 40 (06) : 4922 - 4930
[39] A new palladium(II) complex of a functionalized N-heterocyclic carbene: Synthesis, characterization and application in Suzuki-Miyaura cross-coupling reactions
Linninger, Claudia S.
Herdtweck, Eberhardt
Hoffmann, Stephan D.
Herrmann, Wolfgang A.
Kuehn, Fritz E.
JOURNAL OF MOLECULAR STRUCTURE, 2008, 890 (1-3) : 192 - 197
[40] Suzuki-Miyaura cross-coupling of arenediazonium salts with arylboronic acids catalyzed by a recyclable polymer-supported N-heterocyclic carbene-palladium catalyst
Qin, Yuancheng
Wei, Wei
Luo, Meiming
SYNLETT, 2007, (15) : 2410 - 2414

← 1 2 3 4 5 →