Efficient C-S Bond Formation by Direct Functionalization of C(sp3)-H Bond Adjacent to Heteroatoms under Metal-Free Conditions

被引:23
|
作者
Zhao, Feng [1 ,2 ]
Tan, Qi [1 ]
Wang, Dahan [2 ]
Chen, Jinjin [2 ]
Deng, Guo-Jun [2 ,3 ]
机构
[1] Hunan Univ Med, Key Lab Dong Med Hunan Prov, Sch Pharmaceut Sci, Huaihua 418000, Peoples R China
[2] Xiangtan Univ, Key Lab Environmentally Friendly Chem & Applicat, Key Lab Green Organ Synth & Applicat Hunan Prov, Minist Educ,Coll Chem, Xiangtan 411105, Peoples R China
[3] Chinese Acad Sci, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China
基金
中国国家自然科学基金;
关键词
C(sp(3))-H functionalization; C-S bond formation; heteroatoms; sodium sulfinates; metal-free; CATALYZED REGIOSELECTIVE SULFENYLATION; CROSS-COUPLING REACTION; H BONDS; SULFONYL HYDRAZIDES; DIRECT THIOLATION; INDOLES; ETHERS; DISULFIDES; ARYLATION; OXIDANT;
D O I
10.1002/adsc.201900666
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A simple and efficient method for the formation of C-S bond via direct functionalization of C(sp(3))-H bond adjacent to heteroatoms was described under metal-free conditions. In this work, stable and easily accessible sodium sulfinates were used as the thiolating agents to afford various aryl thioethers in moderate to excellent yields. Mechanistic explorations show that a radical pathyway is possibly involved during the transformations.
引用
收藏
页码:4075 / 4081
页数:7
相关论文
共 50 条
  • [1] Direct Thiolation of the C(sp3)-H Bond Adjacent to Heteroatoms with Thiols under Alkaline Conditions
    Qin, Hui
    Zhang, Yiwen
    Huang, Ping
    [J]. CHEMISTRYSELECT, 2023, 8 (17):
  • [2] Sulfenylation of C-H Bonds for C-S Bond Formation under Metal-Free Conditions
    Dong, Dao-Qing
    Hao, Shuang-Hong
    Yang, Dao-Shan
    Li, Li-Xia
    Wang, Zu-Li
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (45) : 6576 - 6592
  • [3] Recent Development of Metal-Free Direct Asymmetric Functionalization of Benzylic C(sp3)-H Bond
    Jiang, Xin
    Wang, Sidun
    Guo, Guimin
    Lu, Beili
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (04) : 841 - 857
  • [4] Metal-Free Oxidative Functionalization of C(sp3)-H Bond Adjacent to Oxygen and Radical Addition to Olefins
    Zhou, Wei
    Qian, Ping
    Zhao, Jincan
    Fang, Hong
    Han, Jianlin
    Pan, Yi
    [J]. ORGANIC LETTERS, 2015, 17 (05) : 1160 - 1163
  • [5] Functionalization of C(sp3)-h bonds adjacent to oxygen of alcohols under metal-free conditions
    Dong, Dao-Qing
    Hao, Shuang-Hong
    Wang, Zu-Li
    [J]. Mini-Reviews in Organic Chemistry, 2017, 14 (02): : 130 - 135
  • [6] Functionalization of C(sp3)-H Bonds Adjacent to Oxygen of Alcohols under Metal-free Conditions
    Dong, Dao-Qing
    Hao, Shuang-Hong
    Wang, Zu-Li
    [J]. MINI-REVIEWS IN ORGANIC CHEMISTRY, 2017, 14 (02) : 130 - 135
  • [7] Metal-free Thiolation of C (sp3)-S Bond Adjacent to an Oxygen Atom
    Yan Dong
    Tong Mengliang
    [J]. CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2016, 37 (02): : 269 - 273
  • [8] Metal-free oxidative direct C(sp3)-H bond functionalization of ethers with α,α-diaryl allylic alcohols
    Chu, Xue-Qiang
    Meng, Hua
    Zi, You
    Xu, Xiao-Ping
    Ji, Shun-Jun
    [J]. CHEMICAL COMMUNICATIONS, 2014, 50 (68) : 9718 - 9721
  • [9] Direct intramolecular C(sp3)-H bond sulfonamidation to synthesize benzosultam derivatives under metal-free conditions
    Zhang, He
    Sun, Meng-Chan
    Yin, Li-Ming
    Wei, Donghui
    Song, Mao-Ping
    Yang, Dandan
    Niu, Jun-Long
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (24) : 6888 - 6894
  • [10] Recent advances in sulfenylation of C(sp3)-H bond under transition metal-free conditions
    Xin-Ming Xu
    De-Mao Chen
    Zu-Li Wang
    [J]. Chinese Chemical Letters, 2020, 31 (01) : 49 - 57