Rh(III)-Catalyzed Oxidative Olefination of N-(1-Naphthyl)sulfonamides Using Activated and Unactivated Alkenes

被引:96
|
作者
Li, Xuting [1 ,2 ]
Gong, Xue [1 ]
Zhao, Miao [1 ]
Song, Guoyong [1 ]
Deng, Jian [2 ]
Li, Xingwei [1 ]
机构
[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
[2] Univ S China, Sch Chem & Chem Engn, Hengyang 421001, Peoples R China
关键词
CATALYZED ORTHO-OLEFINATION; H BOND-CLEAVAGE; ARYL IODIDES; ALKYNES; DERIVATIVES; ARENES; ACIDS; N; N-DIMETHYLFORMAMIDE; FUNCTIONALIZATION; ALKYLATION;
D O I
10.1021/ol2023856
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Rhodium(III)-catalyzed oxidative olefination of N-(1-naphthyl)sulfonamides has been achieved at the peri position. Three categories of olefins have been successfully applied. Activated olefins reacted to afford five-membered azacycles as a result of oxidative olefination-hydroamination. Unactivated olefins reacted to give the olefination product. 2-fold oxidative C-C and C-N coupling was achieved for allylbenzenes.
引用
收藏
页码:5808 / 5811
页数:4
相关论文
共 45 条
  • [41] Substituent-controlled C-N coupling involved in Rh(III)-catalyzed oxidative [3+2] annulation of 2-acetyl-1-arylhydrazines with maleimides: A DFT study
    Li, Guizhi
    Bi, Siwei
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2020, 927 (927)
  • [42] Palladium-Catalyzed Olefination of 4H-Benzo[d][1,3]oxazin-4-one Derivatives with Activated Alkenes via Preferential Cyclic Imine-N-Directed Aryl C-H Activation
    Panja, Subir
    Maity, Srabani
    Majhi, Biju
    Ranu, Brindaban C.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (33) : 5777 - 5786
  • [43] Rh(III)-Catalyzed Oxidative C-H Activation/Domino Annulation of Anilines with 1,3-Diynes: A Rapid Access to Blue-Emitting Tricyclic N,O-Heteroaromatics
    Qan, Shengyou
    Pu, Xingwen
    Chang, Guanjun
    Huang, Ying
    Yang, Yudong
    ORGANIC LETTERS, 2020, 22 (14) : 5309 - 5313
  • [44] Rh(III)-Catalyzed Domino [4+2] Annulation/Aza-Michael Addition of N-(Pivaloyloxy)benzamides with 1,5-Enynes via C-H Activation: Synthesis of Functionalized Aromathecins
    Reddy, Chada Raji
    Mallesh, Kathe
    Bodasu, Srinivas
    Donthiri, Ramachandra Reddy
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (12): : 7905 - 7915
  • [45] Rh(III)-Catalyzed C(sp2)-H and C(sp2)-C(sp2) Bond Activation of Aryl Oximes with CF3-Imidoyl Sulfoxonium Ylides: Access to N-(2-Cyanoaryl)-3-(Trifluoromethyl)isoquinolin-1(2H)-Imines
    Li, Pinyi
    Chen, Jian
    Yang, Zuguang
    Chen, Zhengkai
    ADVANCED SYNTHESIS & CATALYSIS, 2025,