Palladium-Catalyzed Reductive Heck Hydroarylation of Unactivated Alkenes Using Hydrosilane at Room Temperature

被引:5
|
作者
Shirai, Takahiro [1 ]
Migitera, Yusuke [2 ]
Nakajima, Ryo [1 ]
Kumamoto, Takuya [1 ]
机构
[1] Hiroshima Univ, Grad Sch Biomed & Hlth Sci, Hiroshima 7348553, Japan
[2] Hiroshima Univ, Sch Pharmaceut Sci, Hiroshima 7348553, Japan
来源
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 04期
关键词
ADDITION TYPE REACTION; CARBONYL-COMPOUNDS; ARYL IODIDES; ARYLATION; HYDROGEN; OLEFINS; HYDROCARBOFUNCTIONALIZATION; SUBSTITUTION; ACTIVATION; HALIDES;
D O I
10.1021/acs.joc.3c02488
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reductive Heck hydroarylation of unactivated alkenes has emerged as an essential reaction for regioselective hydroarylation. Herein, we report a palladium-catalyzed reductive Heck hydroarylation of unactivated alkenes under mild conditions with enhanced functional group tolerance using hydrosilane as the reducing reagent. Under the optimal conditions, the alkylarene yields increased, resulting in minimal undesired products. Mechanistic studies using deuterated reagents indicated the involvement of two competing catalytic cycles.
引用
收藏
页码:2787 / 2793
页数:7
相关论文
共 50 条
  • [31] Palladium-catalyzed Mizoroki-Heck-type reactions of [Ph2SRfn][OTf] with alkenes at room temperature
    Wang, Shi-Meng
    Song, Hai-Xia
    Wang, Xiao-Yan
    Liu, Nan
    Qin, Hua-Li
    Zhang, Cheng-Pan
    CHEMICAL COMMUNICATIONS, 2016, 52 (80) : 11893 - 11896
  • [32] An efficient palladium-catalyzed Heck coupling of aryl chlorides with alkenes
    Yi, CY
    Hua, RM
    TETRAHEDRON LETTERS, 2006, 47 (15) : 2573 - 2576
  • [33] Enantioselective Difunctionalization of Alkenes by a Palladium-Catalyzed Heck/Sonogashira Sequence
    Zhou, Lujia
    Li, Sanliang
    Xu, Bing
    Ji, Danting
    Wu, Lizuo
    Liu, Yu
    Zhang, Zhan-Ming
    Zhang, Junliang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (07) : 2769 - 2775
  • [34] Enantioselective difunctionalization of alkenes by a palladium-catalyzed Heck/borylation sequence
    Wu, Yuanqi
    Wu, Lizuo
    Zhang, Zhan-Ming
    Xu, Bing
    Liu, Yu
    Zhang, Junliang
    CHEMICAL SCIENCE, 2022, 13 (07) : 2021 - 2025
  • [35] Palladium-Catalyzed Asymmetric Reductive Heck Reaction of Aryl Halides
    Yue, Guizhou
    Lei, Kaining
    Hirao, Hajime
    Zhou, Jianrong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (22) : 6531 - 6535
  • [36] Palladium-Catalyzed Carbonylative Difunctionalization of Unactivated Alkenes Initiated by Unstabilized Enolates
    Zhang, Pengpeng
    Newhouse, Timothy R.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (39)
  • [37] Palladium-Catalyzed Amide Directed Regioselective γ-Alkenylation of Unactivated Alkenes with Vinylcyclopropanes
    Keerthana, Meledath Sudhakaran
    Jeganmohan, Masilamani
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (42)
  • [38] Palladium-Catalyzed Intramolecular Aminoacetoxylation of Unactivated Alkenes with Hydrogen Peroxide as Oxidant
    Zhu, Haitao
    Chen, Pinhong
    Liu, Guosheng
    ORGANIC LETTERS, 2015, 17 (06) : 1485 - 1488
  • [39] Palladium-Catalyzed Regioselective C-H Iodination of Unactivated Alkenes
    Schreib, Benedikt S.
    Carreira, Erick M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (22) : 8758 - 8763
  • [40] Palladium-Catalyzed Perfluoroalkylative Carbonylation of Unactivated Alkenes: Access to β-Perfluoroalkyl Esters
    Zhang, Youcan
    Geng, Hui-Qing
    Wu, Xiao-Feng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (45) : 24292 - 24298