Visible-Light-Driven Bisfunctionalization of Unactivated Olefins via the Merger of Proton-Coupled Electron Transfer and Carbene Catalysis

被引:47
|
作者
Zhang, Bei [1 ]
Qi, Jian-Qing [1 ]
Liu, Yuhan [1 ]
Li, Zhipeng [1 ]
Wang, Jian [1 ]
机构
[1] Tsinghua Univ, Ctr Basic Mol Sci CBMS, Sch Pharmaceut Sci,Dept Chem, Key Lab Bioorgan Phosphorous Chem & Chem Biol,Min, Beijing 100084, Peoples R China
基金
中国国家自然科学基金;
关键词
CYCLOPROPANATION; ALKYLATION; ESTERS;
D O I
10.1021/acs.orglett.1c03941
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we reported an N-heterocyclic carbene (NHC) and photo-co-catalyzed alkylacylation of olefins in the presence of the versatile synthon diazo ester, providing a new idea for transient radical generation with the only byproduct being N-2. Particularly, this radical process employs traditional carbene precursor diazo esters as the radical source, which is the first case in NHC catalysis. Compared to the previous pathway that produces radicals with large discard fragments, this merged channel possesses great atom economy.
引用
收藏
页码:279 / 283
页数:5
相关论文
共 50 条
  • [1] Hydroalkylation of Unactivated Olefins via Visible-Light-Driven Dual Hydrogen Atom Transfer Catalysis
    Lei, Guangyue
    Xu, Meichen
    Chang, Rui
    Funes-Ardoiz, Ignacio
    Ye, Juntao
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (29) : 11251 - 11261
  • [2] Visible-Light-Driven Transformations of Phenols via Energy Transfer Catalysis
    Fischer, Jerome
    Nun, Pierrick
    Coeffard, Vincent
    SYNTHESIS-STUTTGART, 2020, 52 (11): : 1617 - 1624
  • [3] Proton-coupled electron transfer in catalysis and energy conversion
    Hammes-Schiffer, Sharon
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
  • [4] Crucial Effect of Ti-H Species Generated in the Visible-Light-Driven Transformations: Slowed-Down Proton-Coupled Electron Transfer
    Lin, Yuhan
    Yan, Yan
    Peng, Wei
    Qiao, Xiaofeng
    Huang, Di
    Ji, Hongwei
    Chen, Chuncheng
    Ma, Wanhong
    Zhao, Jincai
    JOURNAL OF PHYSICAL CHEMISTRY LETTERS, 2020, 11 (10): : 3941 - 3946
  • [5] Catalytic Hydroetherification of Unactivated Alkenes Enabled by Proton-Coupled Electron Transfer
    Tsui, Elaine
    Metrano, Anthony J.
    Tsuchiya, Yuto
    Knowles, Robert R.
    Advanced Materials, 2020, 59 (29) : 11943 - 11947
  • [6] Catalytic Hydroetherification of Unactivated Alkenes Enabled by Proton-Coupled Electron Transfer
    Tsui, Elaine
    Metrano, Anthony J.
    Tsuchiya, Yuto
    Knowles, Robert R.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (29) : 11845 - 11849
  • [7] Light-driven proton-coupled electron transfer with photoexcited metal complexes
    Wenger, Oliver S.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
  • [8] Proton-coupled electron transfer in organic synthesis and asymmetric catalysis
    Knowles, Robert
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 249
  • [9] Proton-coupled electron transfer in organic synthesis and asymmetric catalysis
    Knowles, Robert
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
  • [10] Intramolecular Light-Driven Accumulation of Reduction Equivalents by Proton-Coupled Electron Transfer
    Kuss-Petermann, Martin
    Orazietti, Margherita
    Neuburger, Markus
    Hamm, Peter
    Wenger, Oliver S.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (14) : 5225 - 5232