Photoredox-Mediated Synthesis of β-Hydroxydithioacetals from Terminal Alkynes

被引：13
|
作者：
Manzer Manhas, Farah [1 ]
Kumar, Jaswant [2 ]
Raheem, Shabnam [3 ]
Thakur, Pankaj [1 ,4 ]
Rizvi, Masood Ahmad [3 ]
Shah, Bhahwal Ali [2 ]
机构：
[1] Shoolini Univ, Dept Chem, Solan 173212, Himachal Prades, India
[2] CSIR, Indian Inst Integrat Med, Jammu 180001, India
[3] Univ Kashmir, Srinagar 190006, India
[4] Cent Univ Himachal Pradesh, Dept Environm Sci, Dharmshala 176215, India
来源：
CHEMPHOTOCHEM | 2021年 / 5卷 / 03期
关键词：
alkynes; oxidation; photocatalysis; radicals; Rose Bengal; visible light; DIELS-ALDER REACTIONS; THIOL-ENE REACTIONS; BOND FORMATION; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; ALPHA-HYDROXY; C-S; ALKENES; ANION; ACID;
D O I：
10.1002/cptc.202000237
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
A single-step visible light mediated synthesis of beta-hydroxydithioacetals via oxidative coupling of terminal alkynes with thiophenol is reported. Compared to other multistep strategies, this work presents a rare tandem introduction of disulfides and a hydroxy group at the beta-position in one pot. The reaction is enabled by aerial oxidation, features high efficiency and mild conditions, and is extendable to both aliphatic and aromatic alkynes.
引用
收藏
页码：235 / 239
页数：5
相关论文
共 50 条
  • [41] An Efficient Synthesis of Terminal Allenes from Terminal 1-Alkynes
    Kuang, Jinqiang
    Ma, Shengming
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (04): : 1763 - 1765
  • [42] Highly congested spiro-compounds via photoredox-mediated dearomative annulation cascade
    Chao Zhou
    Andrey Shatskiy
    Azamat Z. Temerdashev
    Markus D. Kärkäs
    Peter Dinér
    Communications Chemistry, 5
  • [43] Photoredox-Mediated Routes to Radicals: The Value of Catalytic Radical Generation in Synthetic Methods Development
    Matsui, Jennifer K.
    Lang, Simon B.
    Heitz, Drew R.
    Molander, Gary A.
    ACS CATALYSIS, 2017, 7 (04): : 2563 - 2575
  • [44] Photoredox Catalyzed Thioformylation of Terminal Alkynes Using Nitromethane as a Formyl Source
    Bhat, Muneer-ul-Shafi
    Ganie, Majid Ahmad
    Rizvi, Masood Ahmad
    Raheem, Shabnam
    Shah, Bhahwal Ali
    ORGANIC LETTERS, 2022, 24 (36) : 6658 - 6663
  • [45] Reductive hydrobenzylation of terminal alkynes via photoredox and nickel dual catalysis
    Zhao, Xian
    Zhu, Shengqing
    Qing, Feng-Ling
    Chu, Lingling
    CHEMICAL COMMUNICATIONS, 2021, 57 (74) : 9414 - 9417
  • [46] Synthesis of Tetrasubstituted Pyrroles from Terminal Alkynes and Imines
    Hu, Yancheng
    Wang, Chunxiang
    Wang, Dongping
    Wu, Fan
    Wan, Boshun
    ORGANIC LETTERS, 2013, 15 (12) : 3146 - 3149
  • [47] Switchable Synthesis of lodoalkynes and Diiodoalkenes from Terminal Alkynes
    Chen, Suo
    Zhang, Xiaowei
    Zhao, Hui
    Guo, Xiaohong
    Hu, Xiangguo
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2018, 38 (05) : 1172 - 1176
  • [48] SYNTHESIS OF FUNCTIONALIZED VINYL TRIFLATES FROM TERMINAL ALKYNES
    CRISP, GT
    MEYER, AG
    SYNTHESIS-STUTTGART, 1994, (07): : 667 - 668
  • [49] A new synthesis of α-phenylseleno γ- and δ-lactones from terminal alkynes
    Tiecco, M
    Testaferri, L
    Temperini, A
    Bagnoli, L
    Marini, F
    Santi, C
    SYNLETT, 2003, (05) : 655 - 658
  • [50] Efficient Photoredox-Mediated C-C Coupling Organic Synthesis and Hydrogen Production over Engineered Semiconductor Quantum Dots
    Qi, Ming-Yu
    Li, Yue-Hua
    Anpo, Masakazu
    Tang, Zi-Rong
    Xu, Yi-Jun
    ACS CATALYSIS, 2020, 10 (23) : 14327 - 14335
12345