Direct Thiolation of the C(sp3)-H Bond Adjacent to Heteroatoms with Thiols under Alkaline Conditions

被引:1
|
作者
Qin, Hui [1 ]
Zhang, Yiwen [1 ,2 ]
Huang, Ping [1 ,2 ]
机构
[1] Hangzhou Med Coll, Zhejiang Prov Peoples Hosp, Affiliated Peoples Hosp, Clin Pharm Ctr,Dept Pharm, Hangzhou 310014, Zhejiang, Peoples R China
[2] Key Lab Endocrine Gland Dis Zhejiang Prov, Hangzhou 310014, Zhejiang, Peoples R China
来源
CHEMISTRYSELECT | 2023年 / 8卷 / 17期
关键词
C(sp(3))-S cross-coupling; thiols; ethers; alkaline conditions; radical process; AUTO-OXIDATIVE HYDROXYSULFENYLATION; C-H BONDS; ETHERS; FUNCTIONALIZATION; ALPHA-C(SP(3))-H; DISULFIDES; ARYL;
D O I
10.1002/slct.202300966
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Herein, an operationally facile method for the construction of C-S bond through direct functionalization of C (sp(3))-H bond adja-cent to heteroatoms with thiols has been developed under weakly alkaline conditions. This methodology provides a convenient and efficient strategy to synthesize various aryl thioethers using a cheap and common solvent and base in moderate to good yields. The mechanistic studies indicate that a radical process is possibly involved and the sulfur radical (RS center dot) may be a reactive species during the transformations.
引用
收藏
页数:5
相关论文
共 50 条
  • [1] Efficient C-S Bond Formation by Direct Functionalization of C(sp3)-H Bond Adjacent to Heteroatoms under Metal-Free Conditions
    Zhao, Feng
    Tan, Qi
    Wang, Dahan
    Chen, Jinjin
    Deng, Guo-Jun
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (17) : 4075 - 4081
  • [2] Direct sp3 C-H bond activation adjacent to nitrogen in heterocycles
    Campos, Kevin R.
    CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) : 1069 - 1084
  • [3] Metal-free Thiolation of C (sp3)-S Bond Adjacent to an Oxygen Atom
    Yan Dong
    Tong Mengliang
    CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2016, 37 (02): : 269 - 273
  • [4] TBHP-mediated oxidative thiolation of an sp3 C-H bond adjacent to a nitrogen atom in an amide
    Tang, Ri-Yuan
    Xie, Ye-Xiang
    Xie, Yi-Li
    Xiang, Jian-Nan
    Li, Jin-Heng
    CHEMICAL COMMUNICATIONS, 2011, 47 (48) : 12867 - 12869
  • [5] Rh-Catalyzed Direct Amination of Unactivated C(sp3)-H bond with Anthranils Under Mild Conditions
    Tang, Conghui
    Zou, Miancheng
    Liu, Jianzhong
    Wen, Xiaojin
    Sun, Xiang
    Zhang, Yiqun
    Jiao, Ning
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (32) : 11165 - 11169
  • [6] Nickel-Catalyzed Direct Thiolation of C(sp3)-H Bonds in Aliphatic Amides
    Wang, Xie
    Qiu, Renhua
    Yan, Chunyang
    Reddy, Vutukuri Prakash
    Zhu, Longzhi
    Xu, Xinhua
    Yin, Shuang-Feng
    ORGANIC LETTERS, 2015, 17 (08) : 1970 - 1973
  • [7] Nickel-catalyzed direct thiolation of unactivated C(sp3)-H bonds with disulfides
    Yan, Sheng-Yi
    Liu, Yue-Jin
    Liu, Bin
    Liu, Yan-Hua
    Zhang, Zhuo-Zhuo
    Shi, Bing-Feng
    CHEMICAL COMMUNICATIONS, 2015, 51 (34) : 7341 - 7344
  • [8] 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
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (24) : 6888 - 6894
  • [9] Catalytic alkylation of unactivated C(sp3)-H bonds for C(sp3)-C(sp3) bond formation
    Chen, Zhen
    Rong, Meng-Yu
    Nie, Jing
    Zhu, Xue-Feng
    Shi, Bing-Feng
    Ma, Jun-An
    CHEMICAL SOCIETY REVIEWS, 2019, 48 (18) : 4921 - 4942
  • [10] Direct Allylic C(sp3)-H Thiolation with Disulfides via Visible Light Photoredox Catalysis
    Kim, Jungwon
    Kang, Byungjoon
    Hong, Soon Hyeok
    ACS CATALYSIS, 2020, 10 (11) : 6013 - 6022