Nickel/photoredox dual catalyzed arylalkylation of nonactivated alkenes

被引:12
|
作者
Gao, Yuxi [1 ]
Gao, Lijuan [1 ]
Zhu, Endiao [1 ]
Yang, Yunhong [1 ]
Jie, Mi [1 ]
Zhang, Jiaqian [1 ]
Pan, Zhiqiang [1 ]
Xia, Chengfeng [1 ]
机构
[1] Yunnan Univ, Yunnan Prov Ctr Res & Dev Nat Prod, Sch Pharm, Key Lab Med Chem Nat Resource,Minist Educ, Kunming 650500, Peoples R China
基金
中国国家自然科学基金;
关键词
SINGLE-ELECTRON TRANSMETALATION; PHOTOREDOX-CATALYSIS; NICKEL; DICARBOFUNCTIONALIZATION; DERIVATIVES; DIFUNCTIONALIZATION; LIGANDS; SERIES;
D O I
10.1038/s41467-023-43748-4
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
Alkene dicarbofunctionalization is an efficient strategy and operation-economic fashion for introducing complexity in molecules. A nickel/photoredox dual catalyzed arylalkylation of nonactivated alkenes for the simultaneous construction of one C(sp3)-C(sp3) bond and one C(sp3)-C(sp2) bond has been developed. The mild catalytic method provided valuable indanethylamine derivatives with wide substrate scope and good functional group compatibility. An enantioselective dicarbofunctionalization was also achieved with pyridine-oxazoline as a ligand. The efficiency of metallaphotoredox dicarbofunctionalization was demonstrated for the concise synthesis of pharmaceutically active compounds. Dicarbofunctionalization of nonactivated alkenes is a simple way to rapidly build molecular complexity, but these transformations have not been extensively explore under metallaphotoredox conditions. Here, the authors develop a nickel/photoredox dual catalytic system for arylalkylation of alkenes.
引用
收藏
页数:9
相关论文
共 50 条
  • [21] Elaborating azaaryl alkanes enabled by photoredox/palladium dual catalyzed dialkylation of azaaryl alkenes
    Li, Yunqiang
    Huang, Yongxian
    Li, Sinuo
    Huang, He
    Jiao, Zhiwei
    CHINESE CHEMICAL LETTERS, 2025, 36 (04)
  • [22] Photoredox/Copper Dual-Catalyzed Three-Component Perfluoroalkyl Trifluoromethylthiolation of Alkenes
    Guo, Kang
    Liu, Shaomian
    Yang, Yutong
    Xu, Fang
    Lu, Yongchao
    Shang, Jiayi
    Song, Aizhen
    ORGANIC LETTERS, 2025, 27 (08) : 1994 - 1998
  • [23] Photoredox-Catalyzed Difunctionalization of Alkenes with Sulfilimines
    Yu, Tingwei
    Jin, Zhe
    Ji, Yan
    Yang, Aihong
    Jia, Penghao
    ORGANIC LETTERS, 2024, 26 (37) : 7944 - 7948
  • [24] Photoredox Catalyzed Intramolecular Fluoroalkylarylation of Unactivated Alkenes
    Zhang, Zuxiao
    Martinez, Henry
    Dolbier, William R.
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (05): : 2589 - 2598
  • [25] Palladium-Catalyzed Oxidative Arylalkylation of Unactivated Alkenes: Dual C-H Bond Cleavage of Anilines and Acetonitrile
    Zhang, Hao
    Chen, Pinhong
    Liu, Guosheng
    SYNLETT, 2012, (19) : 2749 - 2752
  • [26] A Dual Cobalt and Photoredox Catalysis for Hydrohalogenation of Alkenes
    Shibutani, Shotaro
    Nagao, Kazunori
    Ohmiya, Hirohisa
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (07) : 4375 - 4379
  • [27] Nickel/Photoredox Dual-Catalyzed Regiodivergent Aminoalkylation of Unactivated Alkyl Halides
    Wang, Wenlong
    Yan, Xueyuan
    Ye, Fu
    Zheng, Songlin
    Huang, Genping
    Yuan, Weiming
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (42) : 23385 - 23394
  • [28] Developments in Photoredox/Nickel Dual-Catalyzed 1,2-Difunctionalizations
    Badir, Shorouk O.
    Molandert, Gary A.
    CHEM, 2020, 6 (06): : 1327 - 1339
  • [29] Transition-Metal-Catalyzed Cyclopropanation of Nonactivated Alkenes in Dibromomethane with Triisobutylaluminum
    Brunner, Gerhard
    Elmer, Susanne
    Schroeder, Fridtjof
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (24) : 4623 - 4633
  • [30] Photoredox catalyzed hydroazolylation of alkenes via phosphoranyl radicals
    Zhu, Fan
    Qiao, Zhi
    He, Na
    Nong, Chunxiao
    He, Qiping
    Xi, Meilan
    Song, Xizhong
    Lin, Jun
    Chen, Jingbo
    Jin, Yi
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (10) : 2839 - 2844