Metal-free photo-induced radical C-P and C-S bond formation for the synthesis of 2-phosphoryl benzothiazoles

被引：54
|
作者：
Yang, Wenchao [1 ]
Li, Bing [1 ]
Zhang, Mingming [1 ]
Wang, Shuang [1 ]
Ji, Yigang [2 ]
Dong, Sa [1 ]
Feng, Jianguo [1 ]
Yuan, Shuzhong [1 ]
机构：
[1] Yangzhou Univ, Guangling Coll & Inst Pesticide, Sch Hort & Plant Protect, Yangzhou 225009, Jiangsu, Peoples R China
[2] Jiangsu Second Normal Univ, Dept Life Sci & Chem, Jiangsu Key Lab Biofuct Mol, Nanjing 210013, Peoples R China
来源：
CHINESE CHEMICAL LETTERS | 2020年 / 31卷 / 05期
基金：
中国博士后科学基金;
关键词：
Phosphorylation; Photo-induced; Isocyanides; Radical cascade reaction; H-Phosphorus oxides; H-PHOSPHINE OXIDES; FREE DIRECT DIFUNCTIONALIZATION; VISIBLE-LIGHT PHOTOCATALYSIS; BETA-KETOPHOSPHINE OXIDES; OXIDATIVE CYCLIZATION; CASCADE REACTION; FUNCTIONALIZATION; ALKYNES; ACIDS; DERIVATIVES;
D O I：
10.1016/j.cclet.2019.10.022
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We reveal here a visible-light promoted phosphorylation of 2-isocyanoaryl thioethers for the first time with concomitant C(sp(3))-S bond cleavage and imidoyl C-S formation. Additionally, this method features the use of 3 mol% organic dye Rose Bengal as the photocatalyst without external transition-metal or peroxide oxidants, and provides a novel and environmentally friendly approach for the preparation of a variety of 2-phosphoryl benzothiazoles in moderate to good yields. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
引用
收藏
页码：1313 / 1316
页数：4
相关论文
共 50 条
  • [1] Metal-free photo-induced radical C-P and C-S bond formation for the synthesis of 2-phosphoryl benzothiazoles
    Wenchao Yang
    Bing Li
    Mingming Zhang
    Shuang Wang
    Yigang Ji
    Sa Dong
    Jianguo Feng
    Shuzhong Yuan
    [J]. Chinese Chemical Letters, 2020, 31 (05) : 1313 - 1316
  • [2] Metal-Free Synthesis of 2-Substituted (N, O, C) Benzothiazoles via an Intramolecular C-S Bond Formation
    Feng, Enguang
    Huang, He
    Zhou, Yu
    Ye, Deju
    Jiang, Hualiang
    Liu, Hong
    [J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (04): : 422 - 429
  • [3] Metal-Free, Visible-Light-Promoted Synthesis of 3-Phosphorylated Coumarins via Radical C-P/C-C Bond Formation
    Liu, Dan
    Chen, Jian-Qiang
    Wang, Xing-Zhi
    Xu, Peng-Fei
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (16) : 2773 - 2777
  • [4] Metal-Free Synthesis of S-Aryldithiocarbamates: Aryl C-S Bond Formation at Room Temperature†
    Madassery, Geo Paul
    Vageesh, M.
    Panja, Subir
    Hima, P.
    Dey, Raju
    [J]. CHEMISTRYSELECT, 2022, 7 (28):
  • [5] Metal-Free Visible-light Mediated C-S Bond Formation
    Sahoo, Ashish Kumar
    Barik, Dinabandhu
    Dam, Binoyargha
    Patel, Bhisma K.
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 12 (08)
  • [6] Electrochemical intramolecular dehydrogenative C-S bond formation for the synthesis of benzothiazoles
    Wang, Pan
    Tang, Shan
    Lei, Aiwen
    [J]. GREEN CHEMISTRY, 2017, 19 (09) : 2092 - 2095
  • [7] Facile synthesis of benzo[b]thiophenes via metal-free radical-triggered intramolecular C-S bond formation
    Fan, Wei
    Chen, Kwong-Yuen
    Chen, Qi-Peng
    Li, Guigen
    Jiang, Bo
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (31) : 6493 - 6499
  • [8] Metal-Free C-S Bond Formation in Elemental Sulfur and Cyclobutanol Derivatives: The Synthesis of Substituted Thiophenes
    Wu, Mingzhong
    Yan, Chaoxian
    Zhuang, Daijiao
    Yan, Rulong
    [J]. ORGANIC LETTERS, 2022, 24 (29) : 5309 - 5313
  • [9] Facile [2,3]-rearrangements of difluoroallylic alcohols with C-P and C-S bond formation
    Blades, K.
    Patel, S. T.
    Percy, J. M.
    Wilkes, R. D.
    [J]. Tetrahedron Letters, 37 (35):
  • [10] Facile [2,3]-rearrangements of difluoroallylic alcohols with C-P and C-S bond formation
    Blades, K
    Patel, ST
    Percy, JM
    Wilkes, RD
    [J]. TETRAHEDRON LETTERS, 1996, 37 (35) : 6403 - 6406
12345