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

被引:16
|
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 50 条
  • [1] New results on the functionalization of terminal alkenes by cross-metathesis reactions
    Blanco, OM
    Castedo, L
    SYNLETT, 1999, (05) : 557 - 558
  • [2] Regioselective ring-opening/cross-metathesis reactions of norbornene derivatives with electron-rich olefins
    Liu, ZQ
    Rainier, JD
    ORGANIC LETTERS, 2005, 7 (01) : 131 - 133
  • [3] Metathesis Reactions of Carbohydrates: Recent Highlights in Cross-Metathesis
    Aljarilla, Ana
    Cristobal Lopez, J.
    Plumet, Joaquin
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (32) : 6123 - 6143
  • [4] Reactions of nitrosovinylphosphonates with electron-rich Alkenes and heterocycles
    Guimaraes, Emanuel
    Lemos, Americo
    Lopes, Marta
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2007, 182 (09) : 2149 - 2155
  • [5] Homometathesis and cross-metathesis coupling of phosphine-borane templates with electron-rich and electron-poor olefins
    Dunne, Katherine S.
    Lee, Sarah E.
    Gouverneur, Veronique
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (24-25) : 5246 - 5259
  • [6] Tandem cross-metathesis/hydrogenation/cyclization reactions by using compatible catalysts
    Cossy, J
    Bargiggia, F
    BouzBouz, S
    ORGANIC LETTERS, 2003, 5 (04) : 459 - 462
  • [7] COMPETITIVE CYCLOPROPANATION AND CROSS-METATHESIS REACTIONS OF ALKENES CATALYZED BY DIRUTHENIUM TETRAKIS CARBOXYLATES
    NOELS, AF
    DEMONCEAU, A
    CARLIER, E
    HUBERT, AJ
    MARQUEZSILVA, RL
    SANCHEZDELGADO, RA
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (12) : 783 - 784
  • [8] ENOL ETHERS .7. REACTIONS OF ALDEHYDES WITH ELECTRON-RICH ALKENES
    EFFENBERGER, F
    MAIER, R
    ANNALEN DER CHEMIE-JUSTUS LIEBIG, 1969, 729 (DEC): : 246 - +
  • [9] Convenient criterion for the distinction between electrophilic and electron transfer reactions of electron-rich alkenes
    Bauld, NL
    Aplin, JT
    Yueh, W
    Endo, S
    Loving, A
    JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 1998, 11 (01) : 15 - +
  • [10] Recent Advances in C-H Bond Functionalization/Cyclization Involving Imines
    Chen, Xun
    Bai, Lili
    Zeng, Wei
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2018, 38 (08) : 1859 - 1871