Palladium-Catalyzed Intermolecular Polarity-Mismatched Addition of Unactivated Alkyl Radicals to Unactivated Alkenes

被引：33
|
作者：
Wu, Xiaojin [1 ]
Xiao, Guanlin [1 ,2 ]
Ding, Yalan [1 ]
Zhan, Ying [1 ]
Zhao, Yao [1 ]
Chen, Rizhi [3 ]
Loh, Teck-Peng [4 ]
机构：
[1] Nanjing Tech Univ, Inst Adv Synth, Sch Chem & Mol Engn, Nanjing 211816, Peoples R China
[2] Guangdong Prov Engn Technol Res Inst Tradit Chine, Guangzhou 510095, Peoples R China
[3] Nanjing Tech Univ, State Key Lab Mat Oriented Chem Engn, Nanjing 211816, Peoples R China
[4] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637616, Singapore
来源：
ACS CATALYSIS | 2020年 / 10卷 / 23期
基金：
中国国家自然科学基金;
关键词：
polarity-mismatched radical addition; unactivated alkenes; heteropolycycles; inert C(sp(3))-C(sp(3)) bond formation; reverse cascade addition process; HECK-TYPE REACTION; C-H ALKYLATIONS; INDOLE-DERIVATIVES; FUNCTIONALIZATION; SECONDARY; HALIDES; OLEFINS; DICARBOFUNCTIONALIZATION; ALKYLARYLATION; ROUTE;
D O I：
10.1021/acscatal.0c04013
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 palladium-catalyzed intermolecular polarity-mismatched addition of unactivated alkyl radicals to unactivated alkenes was developed for the first time. In the two-component dicarbofunctionalization, a variety of primary, secondary, and tertiary unactivated alkyl halides regioselectively reacted with various unactivated olefins. A series of structurally complex heteropolycycles decorated with a quaternary carbon center have been efficiently synthesized.
引用
收藏
页码：14107 / 14116
页数：10
相关论文
共 50 条
  • [1] Nonactivated Aziridine Synthesis by Intermolecular Polarity-Mismatched Carboamination of Unactivated Alkenes with Unactivated Alkyl Halides
    Wu, Linlin
    Li, Lei
    Zhao, Yao
    Rui, Jiacheng
    Zhan, Ying
    Zhang, Ling
    Chen, Rizhi
    Zhou, Jianrong Steve
    Zhu, Chenjie
    Wu, Xiaojin
    ORGANIC LETTERS, 2024, : 5609 - 5613
  • [2] An Intermolecular Palladium-Catalyzed Diamination of Unactivated Alkenes
    Iglesias, Alvaro
    Perez, Edwin G.
    Muniz, Kilian
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (44) : 8109 - 8111
  • [3] A chemoselective radical cascade polarity-mismatched silylarylation of unactivated alkenes
    Liu, Liang
    Yang, Xiao
    Tong, Jinghui
    Zhu, Huajie
    Ouyang, Lu
    Luo, Renshi
    Liao, Jianhua
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (23): : 6700 - 6705
  • [4] Asymmetric Palladium-Catalyzed Aminochlorination of Unactivated Alkenes
    Wang, Zhigang
    Hou, Chuanqi
    Chen, Pinhong
    ORGANIC LETTERS, 2023, 25 (15) : 2685 - 2690
  • [5] Enantioselective palladium-catalyzed diarylation of unactivated alkenes
    Ju, Baihang
    Chen, Shigui
    Kong, Wangqing
    CHEMICAL COMMUNICATIONS, 2019, 55 (95) : 14311 - 14314
  • [6] Palladium-Catalyzed Intramolecular Aminofluorination of Unactivated Alkenes
    Wu, Tao
    Yin, Guoyin
    Liu, Guosheng
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (45) : 16354 - +
  • [7] Palladium-catalyzed intermolecular alkynylcarbonylation of unactivated alkenes: easy access to β-alkynylcarboxylic esters
    Li, Xiang
    Chen, Pinhong
    Liu, Guosheng
    CHEMICAL COMMUNICATIONS, 2022, 58 (15) : 2544 - 2547
  • [8] Palladium-catalyzed alkoxycarbonylation of unactivated alkyl bromides
    Sargent, Brendon
    Alexanian, Erik
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [9] Palladium-catalyzed heteroallylation of unactivated alkenes - synthesis of citalopram
    Hewitt, Joanne F. M.
    Williams, Lewis
    Aggarwal, Pooja
    Smith, Craig D.
    France, David J.
    CHEMICAL SCIENCE, 2013, 4 (09) : 3538 - 3543
  • [10] Intermolecular Palladium-Catalyzed Oxidative Fluorocarbonylation of Unactivated Alkenes: Efficient Access to β-Fluorocarboxylic Esters
    Qi, Xiaoxu
    Yu, Feng
    Chen, Pinhong
    Liu, Guosheng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (41) : 12692 - 12696
12345