Synthesis of 2-substituted cyclohexene derivatives through cross-coupling reactions via π-allylmetal intermediate using N-heterocyclic carbenes (NHCs) as ligands

被引：2

作者：

Yamazaki, Tetsuro ^{[1
]}

Sato, Yoshihiro ^{[1
]}

机构：

[1] Hokkaido Univ, Fac Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan

来源：

SYNTHESIS-STUTTGART | 2008年 / 17期

基金：

日本学术振兴会;

关键词：

N-heterocyclic carbene (NHC); cross-coupling; Migita-Kosugi-Stille reaction; Kumada-Tamao-Coriiu reaction; palladium; nickel;

D O I：

10.1055/s-2008-1067222

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium- or nickel-catalyzed cross-coupling reactions of 2-substituted cyclohexenes, which are generally less reactive than those having no substituent at the C2 position, with organotin reagents (Migita-Kosugi-Stille coupling) or with Grigard reagents (Kumada-Tamao-Corriu coupling) using a NHC as a ligand was investigated. It was found that NHCs are effective as ligands for these reactions, giving the corresponding cross-coupling products in good yields.

引用

页码：2830 / 2834

页数：5

共 50 条

[1] Recent Advances in the Schiff Bases and N-Heterocyclic Carbenes as Ligands in the Cross-Coupling Reactions: A Comprehensive Review
Kumar, Sumit
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 56 (04) : 1168 - 1230
[2] Synthesis of Highly Substituted Furans via Intermolecular Enynone-Aldehyde Cross-Coupling/Cyclization Catalyzed by N-Heterocyclic Carbenes
Wang, Jie
Zheng, Mingyue
Jia, Qianfa
Ren, Qiao
Wu, Jicheng
ORGANIC LETTERS, 2024, 26 (23) : 4868 - 4872
[3] Cross-coupling reactions catalyzed by iron group metals and n-heterocyclic carbenes via nonconventional reaction mechanisms
Hatakeyama T.
Ishizuka K.
Nakamura M.
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, 2011, 69 (11): : 1282 - 1298
[4] Cross-Coupling Reactions Catalyzed by Iron Group Metals and N-Heterocyclic Carbenes via Nonconventional Reaction Mechanisms
Hatakeyama, Takuji
Ishizuka, Kentaro
Nakamura, Masaharu
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2011, 69 (11) : 1282 - 1298
[5] Palladium complexes of N-heterocyclic carbenes as catalysts for cross-coupling reactions - A synthetic chemist's perspective
Kantchev, Eric Assen B.
O'Brien, Christopher J.
Organ, Michael G.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (16) : 2768 - 2813
[6] Sonogashira-type cross-coupling reactions catalyzed by copper complexes of pincer N-heterocyclic carbenes
Domyati, Doaa
Latifi, Reza
Tahsini, Laleh
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2018, 860 : 98 - 105
[7] Well-Defined N-Heterocyclic Carbenes-Palladium(II) Precatalysts for Cross-Coupling Reactions
Marion, Nicolas
Nolan, Steven P.
ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (11) : 1440 - 1449
[8] N-heterocyclic carbenes Part 26.: N-heterocyclic carbene complexes of palladium(0):: synthesis and application in the Suzuki cross-coupling reaction
Böhm, VPW
Gstöttmayr, CWK
Weskamp, T
Herrmann, WA
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 595 (02) : 186 - 190
[9] Nickel-Catalyzed Cross-Coupling of Aryl Bromides with Tertiary Grignard Reagents Utilizing Donor-Functionalized N-Heterocyclic Carbenes (NHCs)
Lohre, Claudia
Droege, Thomas
Wang, Congyang
Glorius, Frank
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (22) : 6052 - 6055
[10] A General Approach to N-Heterocyclic Carbenes with a Fused Tetracyclic Core: Ligands for Suzuki-Miyaura Cross-Coupling Reaction
Sutar, Revannath L.
Kumar, Vinod
Shingare, Rahul D.
Thorat, Shridhar
Gonnade, Rajesh
Reddy, D. Srinivasa
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (21) : 4482 - 4486

← 1 2 3 4 5 →