Relay C(sp3)-H bond trifluoromethylthiolation and amidation by visible light photoredox catalysis

被引：2
|
作者：
Liu, Junheng [1 ]
Yang, Suqi [1 ]
Yao, Shunruo [1 ]
Zhu, Chengjian [1 ,2 ,3 ]
Liu, Yong [4 ]
Li, Weipeng [1 ]
Xie, Jin [1 ,5 ]
机构：
[1] Nanjing Univ, Chem & Biomed Innovat Ctr ChemBIC, Jiangsu Key Lab Adv Organ Mat, State Key Lab Coordinat Chem,Sch Chem & Chem Engn, Nanjing 210023, Peoples R China
[2] Zhengzhou Univ, Coll Chem, Green Catalysis Ctr, Zhengzhou 450001, Peoples R China
[3] Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
[4] Nanjing Bready Adv Mat Technol Co Ltd, Nanjing 221100, Peoples R China
[5] China Pharmaceut Univ, State Key Lab Nat Med, Nanjing 211198, Peoples R China
来源：
SCIENCE CHINA-CHEMISTRY | 2024年 / 67卷 / 11期
基金：
中国国家自然科学基金;
关键词：
photoredox catalysis; C-H activation; trifluoromethylthiolation; amidation; PCET; C-H BONDS; SILVER(I) TRIFLUOROMETHANETHIOLATE; REAGENTS;
D O I：
10.1007/s11426-024-2259-7
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Selective functionaliz0ation of C(sp(3))-H bonds is a straightforward and practical method to construct complex molecule skeletons. In this field, direct transformation of unactivated C(sp(3))-H bonds into C(sp(3))-SCF3 architectures is still a great challenge. We report a highly selective trifluoromethylthiolation of unactivated aliphatic C(sp(3))-H bonds by combination of proton-coupled electron transfer (PCET) and hydrogen atom transfer (HAT) strategy. A wide range of structurally diverse alkyl trifluoromethyl sulfides are obtained. Furthermore, the use of two different photocatalysts can realize an unprecedented trifluoromethylthiolation and amidation cascade of different C(sp(3))-H bonds. It can afford a good access to bifunctionalized molecules in synthetically useful yields.
引用
收藏
页码：3844 / 3850
页数：7
相关论文
共 50 条
  • [1] Visible light promoted photoredox C(sp3)-H bond functionalization of tetrahydroisoquinolines in flow
    Filipovic, Ana
    Dzambaski, Zdravko
    Vasiljevic-Radovic, Dana
    Bondzic, Bojan P.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (12) : 2668 - 2675
  • [2] Heterocyclization involving benzylic C(sp3)-H functionalization enabled by visible light photoredox catalysis
    Pandey, Ganesh
    Laha, Ramkrishna
    Mondal, Pradip Kumar
    CHEMICAL COMMUNICATIONS, 2019, 55 (65) : 9689 - 9692
  • [3] 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
  • [4] C(sp3)-H Cyanation Promoted by Visible-Light Photoredox/Phosphate Hybrid Catalysis
    Wakaki, Takayuki
    Sakai, Kentaro
    Enomoto, Takafumi
    Kondo, Mio
    Masaoka, Shigeyuki
    Oisaki, Kounosuke
    Kanai, Motomu
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (32) : 8051 - 8055
  • [5] Benzylic C(sp3)-H Functionalization for C-N and C-O Bond Formation via Visible Light Photoredox Catalysis
    Pandey, Ganesh
    Laha, Ramkrishna
    Singh, Deepak
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (16): : 7161 - 7171
  • [6] Directed γ-C(sp3)-H Alkylation of Carboxylic Acid Derivatives through Visible Light Photoredox Catalysis
    Chen, Dian-Feng
    Chu, Tjohn C. K.
    Rovis, Tomislav
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (42) : 14897 - 14900
  • [7] Visible-Light-Promoted Remote C(sp3)-H Amidation and Chlorination
    Qin, Qixue
    Yu, Shouyun
    ORGANIC LETTERS, 2015, 17 (08) : 1894 - 1897
  • [8] Phthalide synthesis through dehydrogenated lactonization of the C(sp3)-H bond by photoredox catalysis
    Liu, Hui
    Liu, Chao
    Chen, Shanyi
    Lai, Qihong
    Lin, Yulin
    Cai, Zhixiong
    Huang, Mingqiang
    Cai, Shunyou
    GREEN CHEMISTRY, 2021, 23 (20) : 8212 - 8216
  • [9] A unified photoredox-catalysis strategy for C(sp3)-H hydroxylation and amidation using hypervalent iodine
    Li, Guo-Xing
    Morales-Rivera, Cristian A.
    Gao, Fang
    Wang, Yaxin
    He, Gang
    Liu, Peng
    Chen, Gong
    CHEMICAL SCIENCE, 2017, 8 (10) : 7180 - 7185
  • [10] C(sp3)-C(sp3) Cross-Coupling of Alkyl Bromides and Ethers Mediated by Metal and Visible Light Photoredox Catalysis
    Santos, Marilia S.
    Correa, Arlene G.
    Paixao, Marcio W.
    Koenig, Burkhard
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (12) : 2367 - 2372
12345