Recent Advances in Transformations Involving Electron-Rich Alkenes: Functionalization, Cyclization, and Cross-Metathesis Reactions

被引:17
作者
Zhou, Fei [1 ]
Li, Meng [1 ]
Jiang, Huanfeng [1 ,2 ]
Wu, Wanqing [1 ,2 ]
机构
[1] South China Univ Technol, Sch Chem & Chem Engn, State Key Lab Luminescent Mat & Dev, Guangzhou 510640, Peoples R China
[2] South China Univ Technol, State Key Lab Pulp & Paper Engn, Guangzhou 510640, Peoples R China
基金
中国国家自然科学基金;
关键词
electron-rich alkene; mono-/difunctionalization reaction; cyclization reaction; cross-metathesis reaction; PALLADIUM-CATALYZED ARYLATION; RING-OPENING/CROSS-METATHESIS; 3+2 METHYLENECYCLOPENTANE ANNULATIONS; REGIOSELECTIVE HECK ARYLATION; VINYL ETHERS; ENOL ETHERS; ALPHA-ARYLATION; NORBORNENE DERIVATIVES; GRIGNARD-REAGENTS; COUPLING REACTION;
D O I
10.1002/adsc.202100585
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Due to the versatile reactivity and molecular complexity, as well as diversity, electron-rich alkenes bearing nitrogen, oxygen, or sulfur atoms have been regarded as versatile reagents in organic synthesis. This review mainly focuses on the recent advances in the reaction development of electron-rich alkenes since 2000, including mono-/difunctionalization reactions, cyclization reactions, and cross-metathesis reactions. Numerous protocols enabling facile and efficient transformations of electron-rich alkenes to valuable compounds have been developed, which are discussed with special emphasis placed on the mechanistic aspects and the synthetic utilities. We hope that this review will help inspire future studies and promote developments in this area.
引用
收藏
页码:4841 / 4855
页数:15
相关论文
共 109 条
[1]   Photoredox-Induced Radical Relay toward Functionalized β-Amino Alcohol Derivatives [J].
An, Xiao-De ;
Jiao, Yon-Yon ;
Zhang, Hao ;
Gao, Yuxiang ;
Yu, Shouyun .
ORGANIC LETTERS, 2018, 20 (02) :401-404
[2]   Dioxygen-promoted regioselective oxidative Heck arylations of electron-rich olefins with arylboronic acids [J].
Andappan, MMS ;
Nilsson, P ;
von Schenck, H ;
Larhed, M .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (16) :5212-5218
[3]   CHELATION-CONTROLLED, PALLADIUM-CATALYZED VINYLIC SUBSTITUTION-REACTIONS OF VINYL ETHERS - 2-ARYLETHANAL EQUIVALENTS FROM ARYL HALIDES [J].
ANDERSSON, CM ;
LARSSON, J ;
HALLBERG, A .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (22) :5757-5761
[4]   REGIOCHEMISTRY OF PALLADIUM-CATALYZED ARYLATION REACTIONS OF ENOL ETHERS - ELECTRONIC CONTROL OF SELECTION FOR ALPHA-ARYLATION OR BETA-ARYLATION [J].
ANDERSSON, CM ;
HALLBERG, A ;
DAVES, GD .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (16) :3529-3536
[5]   SYNTHESIS OF BETA-ARYLVINYL ETHERS BY THE PALLADIUM-CATALYZED REACTION OF AROYL CHLORIDES WITH VINYL ETHERS [J].
ANDERSSON, CM ;
HALLBERG, A .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (02) :235-239
[6]   REGIOSELECTIVE PALLADIUM-CATALYZED ARYLATION OF VINYL ETHERS WITH 4-NITROPHENYL TRIFLATE - CONTROL BY ADDITION OF HALIDE-IONS [J].
ANDERSSON, CM ;
HALLBERG, A .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (09) :2112-2114
[7]  
[Anonymous], 2018, ANGEW CHEM
[8]  
[Anonymous], 2006, ANGEW CHEM INT EDIT
[9]   Highly regioselective internal heck arylation of hydroxyalkyl vinyl ethers by aryl halides in water [J].
Arvela, Riina K. ;
Pasquini, Serena ;
Larhed, Mats .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (17) :6390-6396
[10]   RU(BPY)(3)(2+)-MEDIATED ADDITION OF SE-PHENYL P-TOLUENESELENOSULFONATE TO ELECTRON-RICH OLEFINS [J].
BARTON, DHR ;
CSIBA, MA ;
JASZBERENYI, JC .
TETRAHEDRON LETTERS, 1994, 35 (18) :2869-2872