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

[1] 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
[2] Suzuki-miyaura cross-coupling reactions catalyzed by N-heterocyclic carbene palladium complex
Shi, Ji-Cheng
Cao, Xin-Hua
Zheng, Ying
Jia, Li
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2007, 27 (05) : 666 - 669
[3] Nickel/N-Heterocyclic Carbene Catalysis Catalyzed Enantioselective Suzuki-Miyaura Coupling of Ketones
Kong, Weiyu
Yin, Guoyin
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (04) : 1751 - 1752
[4] Palladium catalyzed Suzuki-Miyaura coupling with aryl chlorides using a bulky phenanthryl N-heterocyclic carbene ligand
Song, C
Ma, YD
Chai, Q
Ma, CQ
Jiang, W
Andrus, MB
TETRAHEDRON, 2005, 61 (31) : 7438 - 7446
[5] N-heterocyclic carbene sulfonamide palladium complexes and their catalytic activities in Suzuki-Miyaura coupling reaction
Zhang, Tao
Wang, Wenfeng
Gu, Xingxing
Shi, Min
ORGANOMETALLICS, 2008, 27 (04) : 753 - 757
[6] 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
[7] Palladium-NHC (NHC = N-heterocyclic Carbene)-Catalyzed Suzuki-Miyaura Cross-Coupling of Alkyl Amides
Wang, Chang-An
Rahman, Md Mahbubur
Bisz, Elwira
Szostak, Roman
Dziuk, Blazej
Szostak, Michal
ACS CATALYSIS, 2022, 12 (04) : 2426 - 2433
[8] N-heterocyclic carbene palladium(II)-catalyzed Suzuki-Miyaura cross coupling of N-acylsuccinimides by C-N cleavage
Wang, Tao
Guo, Jiarui
Wang, Hengjin
Guo, Han
Jia, Dingli
Zhang, Wen
Liu, Lantao
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2018, 877 : 80 - 84
[9] Fine Tuning of Chiral Bis(N-heterocyclic carbene) Palladium Catalysts for Asymmetric Suzuki-Miyaura Cross-Coupling Reactions: Exploring the Ligand Modification
Zhang, Dao
Yu, Jueqin
ORGANOMETALLICS, 2020, 39 (08) : 1269 - 1280
[10] Palladium catalyst coordinated in knitting N-heterocyclic carbene porous polymers for efficient Suzuki-Miyaura coupling reactions
Xu, Shujun
Song, Kunpeng
Li, Tao
Tan, Bien
JOURNAL OF MATERIALS CHEMISTRY A, 2015, 3 (03) : 1272 - 1278

← 1 2 3 4 5 →