Nickel-Catalyzed Sulfonylation of C(sp2)-H Bonds with Sodium Sulfinates

被引:38
作者
Liu, Shuang-Liang [1 ]
Li, Xue-Hong [1 ]
Zhang, Shu-Sheng [1 ]
Hou, Sheng-Kai [1 ]
Yang, Guang-Chao [1 ]
Gong, Jun-Fang [1 ]
Song, Mao-Ping [1 ]
机构
[1] Zhengzhou Univ, Coll Chem & Mol Engn, Henan Key Lab Chem Biol & Organ Chem, Zhengzhou 450001, Peoples R China
基金
中国国家自然科学基金;
关键词
C-H activation; nickel; (pyridin-2-yl) isopropylamine (PIP-amine); sodium sulfinates; sulfonylation; C-H BONDS; BIDENTATE-CHELATION ASSISTANCE; UNACTIVATED C(SP(3))-H BONDS; QUINOLINE N-OXIDES; EFFICIENT SYNTHESIS; ARYLSULFONYL CHLORIDES; COUPLING REACTIONS; AROMATIC AMIDES; DIRECTING GROUP; FUNCTIONALIZATION;
D O I
10.1002/adsc.201700290
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The first nickel-catalyzed ortho-sulfonylation of C(sp(2))-H bonds with sodium sulfinates directed by (pyridin-2-yl) isopropylamine (PIP-amine) is described. This strategy exhibits a broad substrate scope and good functional group tolerance with high monosulfonylation selectivity. Besides arenes and heteroarenes, the reaction can also be extended to alkenes, providing diverse diaryl and alkyl aryl sulfones in high yields. Furthermore, a plausible Ni(I)/Ni(III) mechanism is outlined based on our experimental results and related precedents.
引用
收藏
页码:2241 / 2246
页数:6
相关论文
共 50 条
  • [11] Nickel-Catalyzed C(sp2)-H/C(sp3)-H Oxidative Coupling of Indoles with Toluene Derivatives
    Soni, Vineeta
    Khake, Shrikant M.
    Punji, Benudhar
    ACS CATALYSIS, 2017, 7 (06): : 4202 - 4208
  • [12] Nickel-Catalyzed Decarboxylative Arylation of Heteroarenes through sp2 C-H Functionalization
    Yang, Ke
    Wang, Peng
    Zhang, Cheng
    Kadi, Adnan A.
    Fun, Hoong-Kun
    Zhang, Yan
    Lu, Hongjian
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (34) : 7586 - 7589
  • [13] Nickel-catalyzed direct thiolation of unactivated C(sp3)-H bonds with disulfides
    Yan, Sheng-Yi
    Liu, Yue-Jin
    Liu, Bin
    Liu, Yan-Hua
    Zhang, Zhuo-Zhuo
    Shi, Bing-Feng
    CHEMICAL COMMUNICATIONS, 2015, 51 (34) : 7341 - 7344
  • [14] Pyridine-Directed Palladium-Catalyzed Phosphonation of C(sp2)-H Bonds
    Li, Changkun
    Yano, Takaaki
    Ishida, Naoki
    Murakami, Masahiro
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (37) : 9801 - 9804
  • [15] Cobalt-Catalyzed C(sp2)-H Alkoxylation of Aromatic and Olefinic Carboxamides
    Zhang, Lin-Bao
    Hao, Xin-Qi
    Zhang, Shou-Kun
    Liu, Zhan-Jiang
    Zheng, Xin-Xiang
    Gong, Jun-Fang
    Niu, Jun-Long
    Song, Mao-Ping
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (01) : 272 - 275
  • [16] Nickel-catalyzed dual C(sp2)-H activation of arenes: a new route to diaryl ethers
    Lv, Ningning
    Chen, Zhengkai
    Yu, Shuling
    Liu, Zhanxiang
    Zhang, Yuhong
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (16) : 2224 - 2229
  • [17] Manganese(iii) acetate-mediated direct C(sp2)-H-sulfonylation of enamides with sodium and lithium sulfinates
    Kramer, Philipp
    Krieg, Sara-Cathrin
    Kelm, Harald
    Manolikakes, Georg
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (22) : 5538 - 5544
  • [18] Transition-Metal-Catalyzed Acyloxylation: Activation of C(sp2)-H and C(sp3)-H Bonds
    Moghimi, Setareh
    Mahdavi, Mohammad
    Shafiee, Abbas
    Foroumadi, Alireza
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (20) : 3282 - 3299
  • [19] Easily Accessible Auxiliary for Palladium-Catalyzed Intramolecular Amination of C(sp2)-H and C(sp3)-H Bonds at δ- and ε-Positions
    Wang, Chao
    Chen, Changpeng
    Zhang, Jingyu
    Han, Jian
    Wang, Qian
    Guo, Kun
    Liu, Pei
    Guan, Mingyu
    Yao, Yingming
    Zhao, Yingsheng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (37) : 9884 - 9888
  • [20] Direct C(sp3)-H Sulfonylation of Xanthene Derivatives with Sodium Sulfinates by Oxidative Copper Catalysis
    Song, Qinghao
    Zhao, He
    Sun, Yanping
    Jiang, Huanfeng
    Zhang, Min
    CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (03): : 371 - 377