Metal-Free Oxidative Cross-Dehydrogenative Coupling of Alkenes with Thiophenols

被引:1
|
作者
Li, Chunsheng [1 ]
Liao, Mingjian [1 ]
He, Zhiquan [1 ]
Chen, Yunbing [1 ]
Mai, Jingna [1 ]
Dong, Rui [1 ]
Chen, Junhua [1 ]
Chen, Lianfen [1 ]
机构
[1] Zhaoqing Univ, Sch Environm & Chem Engn, Zhaoqing 526061, Peoples R China
来源
CHEMISTRYSELECT | 2023年 / 8卷 / 20期
基金
中国国家自然科学基金;
关键词
Metal-Free; Cross-Dehydrogenative Coupling; Regioselective; Radical addition; Allylic sulfides; C-H OXYGENATION; BOND FORMATION; GRIGNARD-REAGENTS; GREEN CHEMISTRY; C(SP(3))-H; DDQ; ALLYLATION; CATALYSTS; NITROGEN; HALIDES;
D O I
10.1002/slct.202300845
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel transition-metal-free regioselective allylic C-H thiolation of alkenes has been achieved by cross-dehydrogenative coupling strategy. The present protocol realizes efficient and highly regio- and stereo-selective functionalization of allylic C-H bonds under metal-free conditions, leading to a series of allylic thioethers in good to excellent yields. Moreover, this work features mild reaction conditions, high step- and atom-economy and good functional group tolerance.
引用
收藏
页数:5
相关论文
共 50 条
  • [1] Metal-Free Cross-Dehydrogenative Coupling of Heterocycles with Aldehydes
    Matcha, Kiran
    Antonchick, Andrey P.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (07) : 2082 - 2086
  • [2] An Alternative Metal-Free Aerobic Oxidative Cross-Dehydrogenative Coupling of Sulfonyl Hydrazides with Secondary Phosphine Oxides
    Liu, Teng
    Zhang, Yanqiong
    Yu, Rong
    Liu, Jianjun
    Cheng, Feixiang
    [J]. SYNTHESIS-STUTTGART, 2020, 52 (02): : 253 - 262
  • [3] Metal-free cross-dehydrogenative coupling of benzimidazoles with aldehydes to N-acylbenzimidazoles
    Yu, Lin
    Wang, Min
    Wang, Lei
    [J]. TETRAHEDRON, 2014, 70 (35) : 5391 - 5397
  • [4] Transition Metal-Free Cross-Dehydrogenative Coupling Reaction of Coumarins with Acetonitrile or Acetone
    Zhang, Rongxing
    Jin, Shengzhou
    Liu, Qian
    Lin, Sen
    Yan, Zhaohua
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (21): : 13030 - 13035
  • [5] Cross-Dehydrogenative Coupling of Dithiolanes with Ketones and Indoles under Metal-Free Conditions
    Singh, Kamal Nain
    Singh, Paramjit
    Singh, Pushpinder
    Maheshwary, Yogita
    Kessar, Satinder V.
    Batra, Aanchal
    [J]. SYNLETT, 2013, 24 (15) : 1963 - 1967
  • [6] Metal-free oxidative cross-dehydrogenative coupling of quinones with benzylic C(sp3)-H bonds
    Dong, Yu
    Yang, Jian
    He, Shuai
    Shi, Zhi-Chuan
    Wang, Yu
    Zhang, Xiao-Mei
    Wang, Ji-Yu
    [J]. RSC ADVANCES, 2019, 9 (47) : 27588 - 27592
  • [7] A Metal-Free Cross-Dehydrogenative Coupling Reaction of Amides to Access N-Alkylazoles
    Zhu, Zheng
    Wang, Yufeng
    Yang, Mingmeng
    Huang, Ling
    Gong, Jiuhan
    Guo, Shengmei
    Cai, Hu
    [J]. SYNLETT, 2016, 27 (19) : 2705 - 2708
  • [8] A metal-free cross-dehydrogenative coupling of N-carbamoyl tetrahydroisoquinoline by sodium persulfate
    Chen, Wenfang
    Zheng, Hongbo
    Pan, Xinhui
    Xie, Zhiyu
    Zan, Xin
    Sun, Bin
    Liu, Lei
    Lou, Hongxiang
    [J]. TETRAHEDRON LETTERS, 2014, 55 (17) : 2879 - 2882
  • [9] Diacetyl as a "traceless" visible light photosensitizer in metal-free cross-dehydrogenative coupling reactions
    Huang, Chia-Yu
    Li, Jianbin
    Liu, Wenbo
    Li, Chao-Jun
    [J]. CHEMICAL SCIENCE, 2019, 10 (19) : 5018 - 5024
  • [10] Chiral organic contact ion pairs in metal-free catalytic enantioselective oxidative cross-dehydrogenative coupling of tertiary amines to ketones
    Zhang, Gen
    Ma, Yunxia
    Wang, Shoulei
    Kong, Weidong
    Wang, Rui
    [J]. CHEMICAL SCIENCE, 2013, 4 (06) : 2645 - 2651