Three-Component Visible-Light-Induced Palladium-Catalyzed 1,2-Alkyl Carbamoylation/Cyanation of Alkenes

被引:38
|
作者
Jia, Xiangqing [1 ]
Zhang, Ziyan [1 ]
Gevorgyan, Vladimir [1 ]
机构
[1] Univ Texas Dallas, Dept Chem & Biochem, Richardson, TX 75080 USA
基金
美国国家科学基金会; 美国国家卫生研究院;
关键词
difunctionalization; isocyanide; radical; palladium; light-induced; C-H ALKYLATION; CARBENE; DICARBOFUNCTIONALIZATION; ISOCYANIDES; TERTIARY; OLEFINS;
D O I
10.1021/acscatal.1c04183
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A mild visible-light-induced Pd-catalyzed one-pot three-component alkyl-carbamoylation and cyanation of alkenes was developed. This general transformation, which proceeds via the in situ formation of a reactive ketenimine intermediate, allows for a rapid construction of a broad range of valuable amides and nitriles from readily available alkenes, alkyl iodides, and isocyanides. An efficient synthesis of tetrazole and amidine via this approach was also demonstrated.
引用
收藏
页码:13217 / 13222
页数:6
相关论文
共 50 条
  • [1] Visible-Light-Induced Three-Component 1,2-Alkylpyridylation of Alkenes via a Halogen-Atom Transfer Process
    Yu, Weijie
    Wang, Hongyu
    Zhao, Kuang
    Li, Wendong
    Wang, Tao
    Fu, Junkai
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (03): : 1703 - 1708
  • [2] Visible Light Induced Three-Component 1,2-Dicarbofunctionalization of Alkenes and Alkynes
    Mohar, Mrittika
    Ghosh, Sumit
    Hajra, Alakananda
    CHEMICAL RECORD, 2023, 23 (11):
  • [3] Visible-Light-Induced Three-Component Selenofunctionalization of Alkenes: An Aerobic Selenol Oxidation Approach
    Patil, Dilip, V
    Hong, Young Taek
    Kim, Hun Young
    Oh, Kyungsoo
    ORGANIC LETTERS, 2022, : 8465 - 8469
  • [4] Palladium-Catalyzed Three-Component Coupling Reactions: 1,1-Difunctionalization of Activated Alkenes
    Rodriguez, Arantxa
    Moran, Wesley J.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (09) : 1313 - 1316
  • [5] Visible-light-driven three-component reductive 1,2-diarylation of alkenes
    Wang, Tao
    Yu, Weijie
    Lan, Jinping
    Wang, Hongyu
    Jiang, Zhou
    Li, Yang
    Fu, Junkai
    CHEM CATALYSIS, 2023, 3 (05):
  • [6] Visible-Light-Induced Palladium-Catalyzed Dehydrogenative Carbonylation of Amines to Oxalamides
    Meyer, Tim
    Rabeah, Jabor
    Brueckner, Angelika
    Wu, Xiao-Feng
    CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (18) : 5642 - 5647
  • [7] Visible-Light-Induced Three-Component Alkylpyridylation of Alkenes Enabled by Electron Donor-Acceptor Complex
    Shen, Jiaxuan
    Chen, Meijun
    Li, Jincan
    Chen, Yimin
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (14) : 3138 - 3143
  • [8] Nickel-Catalyzed Three-Component 1,2-Carboacylation of Alkenes
    Jin, Shengzhou
    Wang, Lanfen
    Jia, Yinggang
    Ma, Wenbo
    Wang, Dingyi
    MOLECULES, 2024, 29 (18):
  • [9] A Palladium-Catalyzed Three-Component Synthesis of Arylmethylsulfonamides
    Beisel, Tamara
    Manolikakes, Georg
    SYNTHESIS-STUTTGART, 2016, 48 (03): : 379 - 386
  • [10] Palladium-Catalyzed Four-Component Cascade Imidoyl-Carbamoylation of Unactivated Alkenes
    Cheng, Sidi
    Luo, Yu
    Yu, Ting
    Li, Jing
    Gan, Chunfang
    Luo, Shuang
    Zhu, Qiang
    ACS CATALYSIS, 2022, 12 (02) : 837 - 845