Visible-Light-Promoted (Phenylsulfonyl)methylation of Electron-Rich Heteroarenes and N-Arylacrylamides

被引：29
作者：
Liu, Fei [1 ]
Li, Pixu [1 ]
机构：
[1] Soochow Univ, Key Lab Organ Synth Jiangsu Prov, Coll Chem Chem Engn & Mat Sci, 199 RenAi Rd, Suzhou 215123, Jiangsu, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 16期
关键词：
C-H FUNCTIONALIZATION; NUCLEOPHILIC CHARACTER; CATALYZED METHYLATION; HETEROAROMATIC BASES; PHOTOREDOX CATALYSIS; ALKYL RADICALS; OXINDOLES; BOND; CONVENIENT; PEROXIDES;
D O I：
10.1021/acs.joc.6b00689
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Visible-light-promoted radical (phenylsulfonyl)methylation reactions of electron-rich heteroarenes and N-arylacrylamides have been developed starting from bromomethyl phenyl sulfone derivatives. This method provides a mild and efficient access to various (phenylsulfonyl)methylated compounds.
引用
收藏
页码：6972 / 6979
页数：8
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  • [1] The Methylation Effect in Medicinal Chemistry
    Barreiro, Eliezer J.
    Kuemmerle, Arthur E.
    Fraga, Carlos A. M.
    [J]. CHEMICAL REVIEWS, 2011, 111 (09) : 5215 - 5246
  • [2] GENERATION OF RADICALS FROM SULPHOXIDES WITH FENTONS REAGENT - NEW RADICAL ALKYLATION METHOD
    BERTILSS.BM
    GUSTAFSS.B
    KUHN, I
    TORSSELL, K
    [J]. ACTA CHEMICA SCANDINAVICA, 1970, 24 (10): : 3590 - &
  • [3] REACTIONS OF CARBANIONS WITH ELECTRON-ACCEPTORS
    BORDWELL, FG
    CLEMENS, AH
    SMITH, DE
    BEGEMANN, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (08) : 1151 - 1156
  • [4] Tandem Radical Cyclization of N-Arylacrylamides: An Emerging Platform for the Construction of 3,3-Disubstituted Oxindoles
    Chen, Jia-Rong
    Yu, Xiao-Ye
    Xiao, Wen-Jing
    [J]. SYNTHESIS-STUTTGART, 2015, 47 (05): : 604 - 629
  • [5] Visible-Light Photoredox in Homolytic Aromatic Substitution: Direct Arylation of Arenes with Aryl Halides
    Cheng, Yannan
    Gu, Xiangyong
    Li, Pixu
    [J]. ORGANIC LETTERS, 2013, 15 (11) : 2664 - 2667
  • [6] Aerobic Visible-Light Photoredox Radical C-H Functionalization: Catalytic Synthesis of 2-Substituted Benzothiazoles
    Cheng, Yannan
    Yang, Jun
    Qu, Yue
    Li, Pixu
    [J]. ORGANIC LETTERS, 2012, 14 (01) : 98 - 101
  • [7] Peroxide: A Novel Methylating Reagent
    Dai, Qiang
    Jiang, Yan
    Yu, Jin-Tao
    Cheng, Jiang
    [J]. SYNTHESIS-STUTTGART, 2016, 48 (03): : 329 - 339
  • [8] Di-tert Butyl Peroxide-Promoted Sequential Methylation and Intramolecular Aromatization of Isonitriles
    Dai, Qiang
    Yu, Jin-Tao
    Feng, Xiaomei
    Jiang, Yan
    Yang, Haitao
    Cheng, Jiang
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (16) : 3341 - 3346
  • [9] Late-Stage Functionalization of Biologically Active Heterocycles Through Photoredox Catalysis
    DiRocco, Daniel A.
    Dykstra, Kevin
    Krska, Shane
    Vachal, Petr
    Conway, Donald V.
    Tudge, Matthew
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (19) : 4802 - 4806
  • [10] Detour and Direct Induction of Methyl-Containing Chiral Centers via Catalytic C-H or C-C Bond Formation
    Endo, Kohei
    Shibata, Takanori
    [J]. SYNTHESIS-STUTTGART, 2012, 44 (10): : 1427 - 1452
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