Stereoselective synthesis of 1,3,5-trienes from alkynones and allyl carbonyl compounds through C-C σ-bond cleavage under transition-metal-free conditions

被引:1
|
作者
Cheng, Lu [1 ]
Wang, Mengdan [1 ]
Yang, Yajie [1 ]
Wang, Zongkang [1 ]
Zhu, Yilin [1 ]
Kong, Lingkai [2 ]
Li, Yanzhong [1 ]
机构
[1] East China Normal Univ, Sch Chem & Mol Engn, 500 Dongchuan Rd, Shanghai 200241, Peoples R China
[2] Linyi Univ, Sch Chem & Chem Engn, Shuangling Rd, Linyi 276000, Shandong, Peoples R China
来源
ORGANIC CHEMISTRY FRONTIERS | 2022年 / 9卷 / 12期
基金
中国国家自然科学基金;
关键词
CONJUGATED TRIENES; STEREOCONTROLLED SYNTHESIS; RING EXPANSION; INSERTION; ALKYNES; CONVENIENT; ESTERS; OLIGOMERS; ALCOHOLS; ANALOGS;
D O I
10.1039/d2qo00617k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An atom-economical transition-metal-free protocol for the stereoselective synthesis of conjugated trienes has been developed. These transformations were realized through base promoted C-C sigma-bond cleavage reactions of allyl carbonyl compounds. This methodology efficiently constructs a broad range of conjugated trienes with the advantages of mild reaction conditions, low cost and operational simplicity.
引用
收藏
页码:3354 / 3359
页数:6
相关论文
共 50 条
  • [1] Stereoselective synthesis of 1,3,5-trienes from alkynones and allyl carbonyl compounds through C-C σ-bond cleavage under transition-metal-free conditions
    Cheng, Lu
    Wang, Mengdan
    Yang, Yajie
    Wang, Zongkang
    Zhu, Yilin
    Kong, Lingkai
    Li, Yanzhong
    Organic Chemistry Frontiers, 2022, 9 (12) : 3354 - 3359
  • [2] Transition-Metal-Free Multicomponent Approach to Stereoenriched Cyclopentyl-isoxazoles through C-C Bond Cleavage
    Subramanian, Parthasarathi
    Kaliappan, Krishna P.
    CHEMISTRY-AN ASIAN JOURNAL, 2018, 13 (16) : 2031 - 2039
  • [3] Transition-metal-free multinitrogenation of amides by C-C bond cleavage: a new approach to tetrazoles
    Li, Lian-Hua
    Niu, Zhi-Jie
    Li, Ying-Xiu
    Liang, Yong-Min
    CHEMICAL COMMUNICATIONS, 2018, 54 (79) : 11148 - 11151
  • [4] C–F bond activation under transition-metal-free conditions
    HanJun Ai
    Xingxing Ma
    Qiuling Song
    XiaoFeng Wu
    Science China(Chemistry), 2021, (10) : 1630 - 1659
  • [5] C–F bond activation under transition-metal-free conditions
    Han-Jun Ai
    Xingxing Ma
    Qiuling Song
    Xiao-Feng Wu
    Science China(Chemistry), 2021, 64 (10) : 1630 - 1659
  • [6] A metal-free synthesis of diaryl-1,2-diketones by C-C triple bond cleavage of alkynones
    Wang, Xuesong
    Cheng, Guolin
    Shen, Jinhai
    Yang, Xifa
    Wei, Ming-e
    Feng, Yadong
    Cui, Xiuling
    ORGANIC CHEMISTRY FRONTIERS, 2014, 1 (08): : 1001 - 1004
  • [7] Transition-metal-free C-S bond cleavage and transformation of organosulfur compounds
    Yang, Ke
    Li, Qin
    Li, Zhengyi
    Sun, Xiaoqiang
    CHEMICAL COMMUNICATIONS, 2023, 59 (36) : 5343 - 5364
  • [8] Transition-metal-free and base promoted C-C bond formation via C-N bond cleavage of organoammonium salts
    Zhang, Tao
    Wang, Kunyu
    Ke, Yuting
    Tang, Yuanyuan
    Liu, Long
    Huang, Tianzeng
    Li, Chunya
    Tang, Zhi
    Chen, Tieqiao
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (38) : 8237 - 8240
  • [9] Metal-free regioselective C-C bond cleavage in 1,3,5-triazine derivatives of β-diketones
    Kopylovich, Maximilian N.
    Mahmudov, Kamran T.
    Haukka, Matti
    Pombeiro, Armando J. L.
    NEW JOURNAL OF CHEMISTRY, 2014, 38 (02) : 495 - 498
  • [10] C-F bond activation under transition-metal-free conditions
    Ai, Han-Jun
    Ma, Xingxing
    Song, Qiuling
    Wu, Xiao-Feng
    SCIENCE CHINA-CHEMISTRY, 2021, 64 (10) : 1630 - 1659