Transition-Metal-Free Direct Trifluoromethylthiolation and Trifluoromethylsulfoxidation of Electron-Rich Aromatics with CF3SO2Na in the Presence of PCl3

被引:58
|
作者
Zhao, Xia [1 ]
Wei, Aoqi [1 ]
Yang, Bo [1 ]
Li, Tianjiao [1 ]
Li, Quan [2 ]
Qiu, Di [1 ]
Lu, Kui [2 ]
机构
[1] Tianjin Normal Univ, Tianjin Key Lab Struct & Performance Funct Mol, Key Lab Inorgan Organ Hybrid Funct Mat Chem, Coll Chem,Minist Educ, Tianjin 300387, Peoples R China
[2] Tianjin Univ Sci & Technol, Coll Biotechnol, Tianjin 300457, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 17期
基金
美国国家科学基金会;
关键词
HYPERVALENT IODINE REAGENT; SODIUM TRIFLUOROMETHANESULFINATE; SULFONYL HYDRAZIDES; DIFLUOROMETHYLTHIOLATION; THIOLATION; CHLORIDE; PERFLUOROALKYLTHIOLATION; PYRAZOLONES; INDOLES; ACIDS;
D O I
10.1021/acs.joc.7b01226
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new transition-metal-free route for the direct trifluoromethylthiolation and trifluoromethylsulfoxidation of electron-rich aromatics with CF3SO2Na in the presence of PCl3 was developed. Notably, PCl3 was used as a reducing and chlorination reagent. The transition-metal-free protocol utilized cheap and readily available reagents and exhibited good atom economy; therefore, it will serve as an alternative and practical strategy for the trifluoromethylthiolation and trifluoromethylsulfoxidation of electron-rich aromatics.
引用
收藏
页码:9175 / 9181
页数:7
相关论文
共 36 条
  • [21] Transition-metal-free synthesis of CMe2CF3-containing chroman-4-ones via decarboxylative trifluoroalkylation
    Liu, Miao-Chang
    Liu, Wei
    Wu, Hua-Yue
    Zhou, Yun-Bing
    Ding, Qiuping
    Peng, Yiyuan
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (03) : 487 - 491
  • [22] Transition-metal-free direct C-3 alkylation of quinoxalin-2(1H)-ones with ethers
    Yuan, Jinwei
    Fu, Junhao
    Yin, Jihong
    Dong, Zhenhua
    Xiao, Yongmei
    Mao, Pu
    Qu, Lingbo
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (19): : 2820 - 2828
  • [23] Transition-Metal-Free Decarboxylation of 3,3,3-Trifluoro-2,2-dimethylpropanoic Acid for the Preparation of C(CF3)Me2-Containing Heteroarenes
    Liu, Shuai
    Huang, Yangen
    Qing, Feng-Ling
    Xu, Xiu-Hua
    ORGANIC LETTERS, 2018, 20 (17) : 5497 - 5501
  • [24] Mechanistic study of visible light-driven CdS or g-C3N4-catalyzed C-H direct trifluoromethylation of (hetero)arenes using CF3SO2Na as the trifluoromethyl source
    Wang, Lele
    Liu, Ming
    Zha, Wenying
    Wei, Yingcong
    Ma, Xiongfeng
    Xu, Chunwang
    Lu, Chenggang
    Qin, Nanfang
    Gao, Li
    Qiu, Wenzhao
    Sa, Rongjian
    Fu, Xianzhi
    Yuan, Rusheng
    JOURNAL OF CATALYSIS, 2020, 389 : 533 - 543
  • [25] Transition-metal-free direct C-3 cyanation of quinoxalin-2(1H)-ones with ammonium thiocyanate as the "CN" source
    Wang, Jiayang
    Sun, Bin
    Zhang, Liang
    Xu, Tengwei
    Xie, Yuanyuan
    Jin, Can
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (01) : 113 - 118
  • [26] Integrated CO2 capture and selective conversion to syngas using transition-metal-free Na/Al2O3 dual-function material
    Sasayama, Tomone
    Kosaka, Fumihiko
    Liu, Yanyong
    Yamaguchi, Toshiaki
    Chen, Shih-Yuan
    Mochizuki, Takehisa
    Urakawa, Atsushi
    Kuramoto, Koji
    JOURNAL OF CO2 UTILIZATION, 2022, 60
  • [27] Direct Synthesis of 2-Aryl-4-quinolones via Transition-Metal-Free Intramolecular Oxidative C(sp3)-H/C(sp3)-H Coupling
    Hu, Wei
    Lin, Jian-Ping
    Song, Li-Rui
    Long, Ya-Qiu
    ORGANIC LETTERS, 2015, 17 (05) : 1268 - 1271
  • [28] Transition-Metal-Free Radical C(sp3)-C(sp2) and C(sp3)-C(sp3) Coupling Enabled by 2-Azaallyls as Super-Electron-Donors and Coupling-Partners
    Li, Minyan
    Berritt, Simon
    Matuszewski, Lucas
    Deng, Guogang
    Pascual-Escudero, Ana
    Panetti, Grace B.
    Poznik, Michal
    Yang, Xiaodong
    Chruma, Jason J.
    Walsh, Patrick J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (45) : 16327 - 16333
  • [29] Transition metal complexes with sulfur ligands -: 135 -: Electron-rich Fe and Ru complexes with the new trisamine dithiolate ligand 'N3H3S2'-H2 [2,2′-bis(2-mercaptophenylamino)diethylamine]
    Sellmann, D
    Utz, J
    Heinemann, FW
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 1999, (02) : 341 - 348
  • [30] Direct Synthesis of Disubstituted 3-Isoquinolinone Derivatives through the Construction of C-N, C=O, and C(sp2)-C(sp3) Bonds under Transition-Metal-Free Conditions
    Shi, Jianyi
    Chen, Xia
    Huang, Jingyun
    Lu, Yantong
    Yang, Zhendong
    Zhong, Mingli
    Zhu, Zhongzhi
    Chen, Xiuwen
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (03)