Palladium-Catalyzed N-Arylation of Sulfoximines with Aryl Sulfonates

被引:30
|
作者
Yang, Qingjing [1 ]
Choy, Pui Ying [2 ]
Zhao, Qingyang [2 ]
Leung, Man Pan [2 ]
Chan, Hoi Shan [2 ]
So, Chau Ming [1 ]
Wong, Wing-Tak [1 ]
Kwong, Fuk Yee [1 ,2 ]
机构
[1] Hong Kong Polytech Univ, Shenzhen Res Inst SZRI, Shenzhen 518057, Peoples R China
[2] Chinese Univ Hong Kong, Dept Chem, Shatin, Hong Kong, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 18期
基金
中国国家自然科学基金;
关键词
MEDICINAL CHEMISTRY; BOND ACTIVATION; ONE-POT; MESYLATES; LIGANDS; IODIDES; AMINATION; CHLORIDES; BROMIDES; TOSYLATES;
D O I
10.1021/acs.joc.8b01599
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Palladium-catalyzed C-N bond coupling reaction between NH-sulfoximines and aryl halides (e.g., -Br, -I, and -CI and pseudohalides -OTf and -ONf) was successfully achieved. Nevertheless, aryl tosylates/mesylates left much to be achieved. In this report, a general N-arylation of sulfoximines with aryl sulfonates is described. Using Pd(OAc)(2)/MeO-CM-phos complex, the N-aryl sulfoximine products can be obtained in good-to-excellent yields (up to 99%) with good common functional group compatibility. In addition to arene moieties, alkenyl tosylates are shown to be successful coupling partners.
引用
收藏
页码:11369 / 11376
页数:8
相关论文
共 50 条
  • [31] Palladium-catalyzed α-arylation of aldehydes with aryl bromides
    Terao, Y
    Fukuoka, Y
    Satoh, T
    Miura, M
    Nomura, M
    TETRAHEDRON LETTERS, 2002, 43 (01) : 101 - 104
  • [32] Palladium-catalyzed arylation of aryl sulfonamides with cyclohexanones
    Cao, Xiangxiang
    Bai, Yang
    Xie, Yanjun
    Deng, Guo-Jun
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2014, 383 : 94 - 100
  • [33] A Palladium-Catalyzed α-Arylation of Oxindoles with Aryl Tosylates
    Duan, Jindian
    Kwong, Fuk Yee
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (12): : 6468 - 6473
  • [34] Radical N-arylation/alkylation of sulfoximines
    Zhu, Hui
    Teng, Fan
    Pan, Changduo
    Cheng, Jiang
    Yu, Jin-Tao
    TETRAHEDRON LETTERS, 2016, 57 (22) : 2372 - 2374
  • [35] Nickel-Catalyzed N-Arylation of NH-Sulfoximines with Aryl Halides via Paired Electrolysis
    Liu, Dong
    Liu, Zhao-Ran
    Ma, Cong
    Jiao, Ke-Jin
    Sun, Bing
    Wei, Lei
    Lefranc, Julien
    Herbert, Simon
    Mei, Tian-Sheng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (17) : 9444 - 9449
  • [36] Copper-catalyzed denitrogenative N-arylation of sulfoximines and sulfonamides with arylhydrazines
    Dong, Wanrong
    Liu, Chaoyang
    Ma, Xinchi
    Zhang, Yingjun
    Peng, Zhihong
    Xie, Dexun
    An, Delie
    TETRAHEDRON, 2019, 75 (29) : 3886 - 3893
  • [37] Novel application of the palladium-catalyzed N-arylation of hydrazones to a versatile new synthesis of pyrazoles
    Haddad, N
    Baron, J
    TETRAHEDRON LETTERS, 2002, 43 (12) : 2171 - 2173
  • [38] One-pot synthesis of carbazoles by palladium-catalyzed N-arylation and oxidative coupling
    Watanabe, Toshiaki
    Ueda, Satoshi
    Inuki, Shinsuke
    Oishi, Shinya
    Fujii, Nobutaka
    Ohno, Hiroaki
    CHEMICAL COMMUNICATIONS, 2007, (43) : 4516 - 4518
  • [39] One-pot synthesis of carbazoles by palladium-catalyzed N-arylation and oxidative coupling
    Watanabe, Toshiaki
    Inuki, Shinsuke
    Ueda, Satoshi
    Oishi, Shinya
    Ohno, Hiroaki
    Fujii, Nobutaka
    DRUGS OF THE FUTURE, 2007, 32 : 136 - 137
  • [40] Application of the palladium-catalyzed N-arylation of hydrazones to deactivated heteroaryl halides in the synthesis of pyrazoles
    Haddad, N
    Salvagno, A
    Busacca, C
    TETRAHEDRON LETTERS, 2004, 45 (30) : 5935 - 5937