Aryl sulfoxides via palladium-catalyzed arylation of sulfenate anions

被引：94
|
作者：
Maitro, Guillaume [1 ]
Vogel, Sophie [1 ]
Prestat, Guillaume [1 ]
Madec, David [1 ]
Poli, Giovanni [1 ]
机构：
[1] Univ Paris 06, Chim Organ Lab, UMR 7611, CNRS,Inst Chim Mol FR 2769, F-75252 Paris 05, France
来源：
ORGANIC LETTERS | 2006年 / 8卷 / 26期
关键词：
D O I：
10.1021/ol062315a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Palladium- catalyzed arylation of sulfenate anions generated from,- sulfinyl esters can take place under biphasic conditions. This hitherto unknown reaction provides a simple, mild, and efficient route to aryl sulfoxides in good yields. The development of a new pseudo- domino type I procedure involving a sulfinylation followed by a Mirozoki - Heck coupling is also described.
引用
收藏
页码：5951 / 5954
页数：4
相关论文
共 50 条
  • [1] Enantioselective synthesis of aryl Sulfoxides via palladium-catalyzed arylation of sulfenate anions
    Maitro, Guillaume
    Vogel, Sophie
    Sadaoul, Mounel
    Prestat, Guillaume
    Madec, David
    Poli, Giovanni
    ORGANIC LETTERS, 2007, 9 (26) : 5493 - 5496
  • [2] Synthesis of Sulfoxides by Palladium-Catalyzed Arylation of Sulfenate Anions with Aryl Thianthrenium Salts
    Jin, Feifei
    Hu, Qianqian
    Wang, Qiang
    Sun, Jing
    Huang, Kun
    Yan, Chao-Guo
    Han, Ying
    Fei, Haiyang
    Wang, Lei
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (18): : 13319 - 13328
  • [3] Palladium-Catalyzed Arylation of Aryl Sulfenate Anions with Aryl Bromides under Mild Conditions: Synthesis of Diaryl Sulfoxides
    Jiang, Hui
    Jia, Tiezheng
    Zhang, Mengnan
    Walsh, Patrick J.
    ORGANIC LETTERS, 2016, 18 (05) : 972 - 975
  • [4] Palladium-Catalyzed Arylation of Alkyl Sulfenate Anions
    Jia, Tiezheng
    Zhang, Mengnan
    Jiang, Hui
    Wang, Carol Y.
    Walsh, Patrick J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (43) : 13887 - 13893
  • [5] Palladium-Catalyzed Enantioselective Arylation of Aryl Sulfenate Anions: A Combined Experimental and Computational Study
    Jia, Tiezheng
    Zhang, Mengnan
    McCollom, Samuel P.
    Bellomo, Ana
    Montel, Sonia
    Mao, Jianyou
    Dreher, Spencer D.
    Welch, Christopher J.
    Regalado, Erik L.
    Williamson, R. Thomas
    Manor, Brian C.
    Tomson, Neil C.
    Walsh, Patrick J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (24) : 8337 - 8345
  • [6] Preparation of allyl sulfoxides by palladium-catalyzed allylic alkylation of sulfenate anions
    Maitro, Guillaume
    Prestat, Guillaume
    Madec, David
    Poli, Giovanni
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (19): : 7449 - 7454
  • [7] Palladium-catalyzed direct arylation of aryl methyl sulfoxides with aryl halides
    Jia, Tiezheng
    Peraza, Ana I. Bellomo
    Dreher, Spencer D.
    Walsh, Patrick J.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
  • [8] Palladium-Catalyzed Direct Arylation of Methyl Sulfoxides with Aryl Halides
    Jia, Tiezheng
    Bellomo, Ana
    El Baina, Kawtar
    Dreher, Spencer D.
    Walsh, Patrick J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (10) : 3740 - 3743
  • [9] tert-Butyl Sulfoxides: Key Precursors for Palladium-Catalyzed Arylation of Sulfenate Salts
    Gelat, Fabien
    Lohier, Jean-Francois
    Gaumont, Annie-Claude
    Perrio, Stephane
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (09) : 2011 - 2016
  • [10] Palladium-Catalyzed Enantioselective Alkenylation of Sulfenate Anions
    Wu, Chen
    Berritt, Simon
    Liang, Xiaoxia
    Walsh, Patrick J.
    ORGANIC LETTERS, 2019, 21 (04) : 960 - 964
12345