Recent advances in reactions between arynes and organosulfur compounds

被引:70
|
作者
Matsuzawa, Tsubasa [1 ]
Yoshida, Suguru [1 ]
Hosoya, Takamitsu [1 ]
机构
[1] TMDU, Inst Biomat & Bioengn, Lab Chem Biosci, Chiyoda Ku, 2-3-10 Kanda Surugadai, Tokyo 1010062, Japan
关键词
Aryne intermediates; Organosulfurs; Addition reactions; Rearrangement; Diversity-oriented synthesis; C-H ACTIVATION; BOND FORMATION; FACILE ACCESS; TRIARYLSULFONIUM SALTS; STEVENS REARRANGEMENT; EFFICIENT GENERATION; DIRECT THIOAMINATION; MODULAR SYNTHESIS; ARYL TRIFLONES; INSERTION;
D O I
10.1016/j.tetlet.2018.10.031
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The recent progress made on transformations involving the reactions between aryne intermediates and organosulfur compounds has been reviewed. A wide variety of aromatic organosulfurs are now synthesizable by generating arynes in the presence of organosulfur compounds. Organosulfurs have distinctive reactivities with arynes, which depend on the sulfur atom's valence state, that is, S(II), S(IV), and S(VI), as well as the presence or absence of other intra- or intermolecular reactive moieties. These novel transformations have enabled the diversity-oriented synthesis of unique aromatic organosulfurs that were once difficult to prepare by the conventional methods, paving the way for the development of molecules that are beneficial across numerous disciplines, including pharmaceutical science and materials science. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4197 / 4208
页数:12
相关论文
共 50 条
  • [21] Recent Advances in Multicomponent Reactions with Organic and Inorganic Sulfur Compounds
    Tang, Qinqin
    Yin, Xianjie
    Kuchukulla, Ratnakar Reddy
    Zeng, Qingle
    [J]. CHEMICAL RECORD, 2021, 21 (04): : 893 - 905
  • [22] METAL-ION-PROMOTED REACTIONS OF ORGANOSULFUR COMPOUNDS
    SATCHELL, DPN
    [J]. CHEMICAL SOCIETY REVIEWS, 1977, 6 (03) : 345 - 371
  • [23] Recent advances in the dichalcogenation reactions of unsaturated compounds via double functionalization
    Wang, Chang-Sheng
    Xu, Yuan
    Zhou, Yi-Liang
    Zheng, Chun-Ling
    Wang, Guowei
    Sun, Qiao
    [J]. INORGANIC CHEMISTRY FRONTIERS, 2023, 10 (19): : 4972 - 5027
  • [24] Recent advances in the dichalcogenation reactions of unsaturated compounds via double functionalization
    Wang, Chang-Sheng
    Xu, Yuan
    Zhou, Yi-Liang
    Zheng, Chun-Ling
    Wang, Guowei
    Sun, Qiao
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2023,
  • [25] Recent advances in the electrochemical reactions of nitrogen-containing organic compounds
    Kaboudin, Babak
    Behroozi, Milad
    Sadighi, Sepideh
    [J]. RSC ADVANCES, 2022, 12 (47) : 30466 - 30479
  • [26] Recent advances in the chemistry of Rh carbenoids: multicomponent reactions of diazocarbonyl compounds
    Medvedev, J. J.
    Nikolaev, V. A.
    [J]. RUSSIAN CHEMICAL REVIEWS, 2015, 84 (07) : 737 - 757
  • [27] GENERATION AND REACTIONS OF HETEROAROMATIC ARYNES USING HYPERVALENT IODINE COMPOUNDS
    Gondo, Keisuke
    Oyamada, Juzo
    Kitamura, Tsugio
    [J]. HETEROCYCLES, 2015, 90 (01) : 681 - 689
  • [28] Recent Progress in P- and S-Arylation Reactions of Arynes
    Huang, Yuanting
    Chen, Qian
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (12) : 4087 - 4100
  • [29] STUDIES IN ASYMMETRIC SYNTHESIS - HIGHLY STEREOSELECTIVE REACTIONS OF ORGANOSULFUR COMPOUNDS
    ELIEL, EL
    [J]. TETRAHEDRON, 1974, 30 (12) : 1503 - 1513
  • [30] Recent advances in nucleophilic fluorination reactions of organic compounds using Deoxofluor and DAST
    Singh, RP
    Shreeve, JM
    [J]. SYNTHESIS-STUTTGART, 2002, (17): : 2561 - 2578