Recent Advances in the Tandem Difunctionalization of Alkynes: Mechanism-Based Classification

被引:17
|
作者
Gao, Biwen [1 ]
Deng, Danfeng [1 ]
Huang, Dayun [1 ]
Sun, Xiangyu [2 ]
机构
[1] Lishui Univ, Dept Chem, 1 Xueyuan Rd, Lishui City 323000, Zhejiang, Peoples R China
[2] Minist Sci & Technol, Torch High Technol Ind Dev Ctr, 18 Sanlihe Dist, Beijing 100045, Peoples R China
来源
SYNTHESIS-STUTTGART | 2021年 / 53卷 / 19期
关键词
alkynes; difunctionalization; mechanism; radicals; tandem reactions; PALLADIUM-CATALYZED DIFUNCTIONALIZATION; SULFUR-MEDIATED DIFUNCTIONALIZATION; DIRECT VICINAL DIFUNCTIONALIZATION; OXIDATIVE IPSO-ANNULATION; TERMINAL ALKYNES; STEREOSELECTIVE DIFUNCTIONALIZATION; ACTIVATED ALKYNES; PROMOTED DIFUNCTIONALIZATION; RADICAL ADDITION/CYCLIZATION; N-ARYLPROPIOLAMIDES;
D O I
10.1055/a-1486-2158
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Recent advances on the tandem difunctionalization of alkynes in the last decade (2010-2020) are summarized into five categories based on the type of mechanism: (1) radical addition and coupling for the synthesis of polysubstituted ketones and alkenes, (2) electrophilic addition of alkynes, (3) reactions mediated by haloalkynes or copper acetylides, (4) the preparation of cyclic compounds via radical processes, palladium-catalyzed reactions or conjugate additions, and (5) cyclic compounds as intermediates in ring openings. Herein, radical, electrophilic and nucleophilic reactions are discussed in detail. We hope this review will help to promote future research in this area. 1 Introduction 2 Radical Addition and Coupling 3 Electrophilic Addition 4 Reactions Mediated by Haloalkynes or Copper Acetylides 5 Cyclization 6 Cyclization and Ring Opening 7 Conclusions
引用
收藏
页码:3522 / 3534
页数:13
相关论文
共 50 条
  • [41] Recent advances in radical transformations of internal alkynes
    Huang, Min-Hua
    Hao, Wen-Juan
    Li, Guigen
    Tu, Shu-Jiang
    Jiang, Bo
    CHEMICAL COMMUNICATIONS, 2018, 54 (77) : 10791 - 10811
  • [42] Recent advances in electrooxidative radical transformations of alkynes
    Yan Zhang
    Zhenzhi Cai
    Svenja Warratz
    Chanchan Ma
    Lutz Ackermann
    Science China Chemistry, 2023, 66 : 703 - 724
  • [43] Recent advances in difunctionalization of alkenes using pyridinium salts as radical precursors
    Wang, Yanan
    Bao, Yanyang
    Tang, Meifang
    Ye, Zhegao
    Yuan, Zheliang
    Zhu, Gangguo
    CHEMICAL COMMUNICATIONS, 2022, 58 (24) : 3847 - 3864
  • [44] Recent Advances in Ni-Catalyzed Asymmetric Reductive Difunctionalization of Alkenes
    Ping Yuanyuan
    Song Haixia
    Kong Wangqing
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (10) : 3302 - 3321
  • [45] Recent advances on catalytic asymmetric difunctionalization of 1,3-dienes
    Xiong, Yang
    Sun, Youwen
    Zhang, Guozhu
    TETRAHEDRON LETTERS, 2018, 59 (04) : 347 - 355
  • [46] Recent Advances in Organochalcogen Synthesis Based on Reactions of Chalcogen Halides with Alkynes and Alkenes
    Potapov, Vladimir A.
    Musalov, Maxim V.
    Musalova, Maria V.
    Amosova, Svetlana V.
    CURRENT ORGANIC CHEMISTRY, 2016, 20 (02) : 136 - 145
  • [47] Recent Advances in Kernel-Based Graph Classification
    Kriege, Nils M.
    Morris, Christopher
    MACHINE LEARNING AND KNOWLEDGE DISCOVERY IN DATABASES, ECML PKDD 2017, PT III, 2017, 10536 : 388 - 392
  • [48] Recent advances in three-component difunctionalization ofgem-difluoroalkenes
    Liu, Chi
    Zeng, Hao
    Zhu, Chuanle
    Jiang, Huanfeng
    CHEMICAL COMMUNICATIONS, 2020, 56 (72) : 10442 - 10452
  • [49] Mechanisms of Disease: mechanism-based classification of neuropathic pain - a critical analysis
    Finnerup, NB
    Jensen, TS
    NATURE CLINICAL PRACTICE NEUROLOGY, 2006, 2 (02): : 107 - 115
  • [50] Mechanisms of Disease: mechanism-based classification of neuropathic pain—a critical analysis
    Nanna B Finnerup
    Troels S Jensen
    Nature Clinical Practice Neurology, 2006, 2 : 107 - 115