Transition-metal free direct difluoromethylthiolation of electron-rich aromatics with difluoromethanesulfonyl chloride

被引:43
|
作者
Zhao, Xia [1 ]
Wei, Aoqi [1 ]
Li, Tianjiao [1 ]
Su, Zhiyang [1 ]
Chen, Jun [2 ]
Lu, Kui [3 ]
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] Beijing Inst Microchem, Beijing 100091, Peoples R China
[3] Tianjin Univ Sci & Technol, Coll Biotechnol, Tianjin 300457, Peoples R China
来源
ORGANIC CHEMISTRY FRONTIERS | 2017年 / 4卷 / 02期
基金
中国国家自然科学基金;
关键词
ALPHA-FLUORINATED ETHERS; ARYL SULFONYL HYDRAZIDES; SULFENYLATION REAGENTS; DIFLUOROMETHYLATING REAGENT; THIOETHERS; DIFLUOROCARBENE; THIOLATION; AMINES; ACID; PYRAZOLONES;
D O I
10.1039/c6qo00581k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new method for phosphine-mediated difluoromethylthiolation of indole derivatives and other electronrich aromatics including pyrroles, pyrazolones, indolizine, and 1,3,5-trimethoxybenzene was developed using difluoromethanesulfonyl chloride. The additive n-Bu4NI was demonstrated to facilitate this reaction by generating iodine in situ, which could promote this transformation. The use of a transition-metal- free protocol, readily available reagents, and mild reaction conditions makes this protocol more practical than traditional methods.
引用
收藏
页码:232 / 235
页数:4
相关论文
共 50 条
  • [41] Metal-free allylation of electron-rich heteroaryl boronic acids with allylic alcohols
    Li, Xue-Dong
    Xie, Li-Jun
    Kong, De-Long
    Liu, Li
    Cheng, Liang
    [J]. TETRAHEDRON, 2016, 72 (15) : 1873 - 1880
  • [42] Direct Noncatalytic Electrophilic Trifluoroacetylation of Electron-Rich Pyrazoles
    Yarmoliuk, Dmytro V.
    Arkhipov, Viatcheslav V.
    Stambirskyi, Maksym V.
    Dmytriv, Yurii V.
    Shishkin, Oleg V.
    Tolmachev, Andrei A.
    Mykhailiuk, Pavel K.
    [J]. SYNTHESIS-STUTTGART, 2014, 46 (09): : 1254 - 1260
  • [43] Metal-Free Oxidative Cross Coupling of Indoles with Electron-Rich (Hetero)arenes
    Caramenti, Paola
    Nandi, Raj Kumar
    Waser, Jerome
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (40) : 10049 - 10053
  • [44] THE ACTIVATION OF CARBON-DIOXIDE IN TRANSITION-METAL CENTERS - METAL RING CLOSING WITH DICYCLOPENTADIENE IN ELECTRON-RICH NICKEL (0)-COMPLEX MOIETIES AS TOPOSELECTIVE AND STEREOSELECTIVE REACTION
    WALTHER, D
    DINJUS, E
    SIELER, J
    ANDERSEN, L
    LINDQVIST, O
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1984, 276 (01) : 99 - 107
  • [45] Visible-Light Cercosporin Catalyzed Sulfenylation of Electron-Rich Compounds with Thiols under Transition-Metal-Free Conditions
    Hazarika, Sukanya
    Barman, Pranjit
    [J]. CHEMISTRYSELECT, 2020, 5 (37): : 11583 - 11589
  • [46] Solvent-free nitration of electron-rich arenes
    Jagadish, Bhumasamudram
    Hurley, Nathaniel R.
    Mash, Eugene A.
    [J]. SYNTHETIC COMMUNICATIONS, 2017, 47 (24) : 2395 - 2398
  • [47] ACTIVATION OF CARBON-DIOXIDE AT TRANSITION-METAL CENTERS - THE OXIDATIVE COUPLING OF CO2 WITH CARBODIIMIDES AT ELECTRON-RICH NICKEL(0) COMPLEXES
    WALTHER, D
    DINJUS, E
    HERZOG, V
    [J]. ZEITSCHRIFT FUR CHEMIE, 1983, 23 (05): : 188 - 188
  • [48] TRANSITION METAL-METHYLENE COMPLEXES .12. REVERSIBLE PROTONATION OF ELECTRON-RICH METAL-METAL BOND
    HERRMANN, WA
    PLANK, J
    RIEDEL, D
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1980, 190 (02) : C47 - C50
  • [49] ELECTRON-ENERGY LOSS FOR 2 TRANSITION-METAL TRANSITION-METAL GLASSES
    FOILES, CL
    [J]. SOLID STATE COMMUNICATIONS, 1985, 53 (06) : 533 - 536
  • [50] FREE-RADICAL COPOLYMERIZATION OF ELECTRON-RICH VINYL MONOMERS WITH ACRYLONITRILE COMPLEXED TO ZINC-CHLORIDE
    WANG, H
    CHU, G
    SRISIRI, W
    PADIAS, AB
    HALL, HK
    [J]. ACTA POLYMERICA, 1994, 45 (01) : 26 - 35