Iodine-promoted decarboxylative C-S cross-coupling of cinnamic acids with sodium benzene sulfinates

被引:58
作者
Chen, Jie [1 ]
Mao, Jincheng [1 ,2 ]
Zheng, Yang [1 ]
Liu, Defu [1 ]
Rong, Guangwei [1 ]
Yan, Hong [1 ]
Zhang, Cheng [1 ]
Shi, Daqing [1 ]
机构
[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China
[2] Southwest Petr Univ, State Key Lab Oil & Gas Reservoir Geol & Exploita, Chengdu 610500, Peoples R China
关键词
Decarboxylative coupling; Cinnamic acids; Cross-couplings; Sulfinates; Metal-free; BETA-IODOVINYL SULFONES; CARBOXYLIC-ACIDS; VINYL SULFONES; ARYL; FUNCTIONALIZATION; SULFONYLATION; ALKENYLATION; CHLORIDES; SULFIDES; AMIDES;
D O I
10.1016/j.tet.2015.05.115
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We have developed a practical example of metal-free iodine-promoted decarboxyltive couplings between cinnamic acids and sodium benzene sulfinates, which represents an effective synthesis of vinyl sulfones via C-S bond formation reaction. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5059 / 5063
页数:5
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共 46 条
  • [21] Copper-Mediated Oxidative Decarboxylative Coupling of Arylpropiolic Acids with Dialkyl H-Phosphonates in Water
    Li, Xiang
    Yang, Fan
    Wu, Yangjie
    Wu, Yusheng
    [J]. ORGANIC LETTERS, 2014, 16 (03) : 992 - 995
  • [22] Vinyl sulfones: Synthetic preparations and medicinal chemistry applications
    Meadows, D. Christopber
    Gervay-Hague, Jacquelyn
    [J]. MEDICINAL RESEARCH REVIEWS, 2006, 26 (06) : 793 - 814
  • [23] ELIMINATIVE DEOXYGENATION - A FACILE SYNTHESIS OF ALPHA-CYANO AND ALPHA-CARBOALKOXY SUBSTITUTED VINYL SULFIDES
    MILLER, RD
    HASSIG, R
    [J]. TETRAHEDRON LETTERS, 1985, 26 (20) : 2395 - 2398
  • [24] CAN mediated reaction of aryl sulfinates with alkenes and alkynes:: Synthesis of vinyl sulfones, β-iodovinyl sulfones and acetylenic sulfones
    Nair, V
    Augustine, A
    Suja, TD
    [J]. SYNTHESIS-STUTTGART, 2002, (15): : 2259 - 2265
  • [25] Synthesis of 3H-Pyrazolo[3,4-c]isoquinolines and Thieno[3,2-c]isoquinolines via Cascade Imination/Intramolecular Decarboxylative Coupling
    Pandey, Garima
    Bhowmik, Subhendu
    Batra, Sanjay
    [J]. ORGANIC LETTERS, 2013, 15 (19) : 5044 - 5047
  • [26] Copper-Catalyzed Oxidative Decarboxylative Couplings of Sulfoximines and Aryl Propiolic Acids
    Priebbenow, Daniel L.
    Becker, Peter
    Bolm, Carsten
    [J]. ORGANIC LETTERS, 2013, 15 (24) : 6155 - 6157
  • [27] Synthesis of Vinyl Sulfides by Copper-Catalyzed Decarboxylative C-S Cross-Coupling
    Ranjit, Sadananda
    Duan, Zhongyu
    Zhang, Pengfei
    Liu, Xiaogang
    [J]. ORGANIC LETTERS, 2010, 12 (18) : 4134 - 4136
  • [28] Palladium-catalyzed coupling of vinyl tosylates with arylsulfinate salts
    Reeves, Diana C.
    Rodriguez, Sonia
    Lee, Heewon
    Haddad, Nizar
    Krishnamurthy, Dhileep
    Senanayake, Chris H.
    [J]. TETRAHEDRON LETTERS, 2009, 50 (24) : 2870 - 2873
  • [29] Decarboxylative coupling reactions: a modern strategy for C-C-bond formation
    Rodriguez, Nuria
    Goossen, Lukas J.
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) : 5030 - 5048
  • [30] Copper-Catalyzed Decarboxylative Sulfonylation of α,β-Unsaturated Carboxylic Acids
    Rokade, Balaji V.
    Prabhu, Kandikere Ramaiah
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (17) : 8110 - 8117