Synthesis of 1,3-disubstituted bicyclo[1.1.1]pentanes by cross-coupling induced by transition metals - formation of C-C bonds

被引:4
|
作者
Yasukawa, Tomohiro [1 ]
Haheim, Katja S. [1 ]
Cossy, Janine [1 ]
机构
[1] PSL, ESPCI Paris, Mol Macromol Chem & Mat, CNRS, F-75005 Paris, France
关键词
LIQUID-CRYSTALLINE; BRIDGEHEAD; ROUTE; ARYL; SALTS; SCOPE;
D O I
10.1039/d3ob01036h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of 1,3-disubstituted bicyclo[1.1.1]pentanes (BCPs), by forming a C-C bond, can be achieved by cross-coupling reactions using transition metal catalysts. Two main strategies are described to access these 1,3-disubstituted BCPs, either from nucleophilic BCPs or electrophilic BCPs. Mechanisms are included where relevant. The synthesis of 1,3-disubstituted bicyclo[1.1.1]pentanes (BCPs), by forming a C-C bond, can be achieved by cross-coupling reaction using transition metal catalysts.
引用
收藏
页码:7666 / 7680
页数:15
相关论文
共 50 条
  • [21] Transition-metal catalyzed oxidative cross-coupling reactions to form C-C bonds involving organometallic reagents as nucleophiles
    Shi, Wei
    Liu, Chao
    Lei, Aiwen
    CHEMICAL SOCIETY REVIEWS, 2011, 40 (05) : 2761 - 2776
  • [22] Cross-Coupling of Directed C-H and Organometallic Reagents for C-C Bond Formation
    Li, Hua
    Ren, Xiangwei
    Zhao, Wentao
    Tang, Xiangyang
    Wang, Guangwei
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (09) : 2287 - 2302
  • [23] Harmonizing Visible-Light in Green Synthesis: Unrevealing the Brilliance of Metal-Free Cross-Coupling of Unsaturated Hydrocarbons for C-C Bonds Formation
    Patel, Vishwa K.
    Patel, Divyani P.
    Singh, Satish Kumar
    CHEMPHOTOCHEM, 2024, 8 (12):
  • [24] Different C-C coupling reactions of permethyltitanocene and permethylzirconocene with disubstituted 1,3-butadiynes
    Pellny, PM
    Kirchbauer, FG
    Burlakov, VV
    Baumann, W
    Spannenberg, A
    Rosenthal, U
    CHEMISTRY-A EUROPEAN JOURNAL, 2000, 6 (01) : 81 - 90
  • [25] Coupling of Nitrogen Heteroaromatics and Alkanes without Transition Metals: A New Oxidative Cross-Coupling at C-H/C-H Bonds
    Deng, Guojun
    Ueda, Kirika
    Yanagisawa, Shuichi
    Itami, Kenichiro
    Li, Chao-Jun
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (02) : 333 - 337
  • [26] Visible light-induced synthesis of 1,3-disubstituted bicyclo[1.1.1]pentane ketones via cooperative photoredox and N-heterocyclic carbene catalysis
    Gao, Yan
    Zheng, Zicong
    Zhu, Yu
    Xu, Wenhao
    Zhou, Yu
    Yu, Chuanming
    Jiang, Xinpeng
    GREEN CHEMISTRY, 2023, 25 (10) : 3909 - 3915
  • [27] Utilizing a C-C activation/cross-coupling strategy toward the total synthesis of taxagifine
    Wang, Brian
    Wyler, Benjamin
    Sarpong, Richmond
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [28] Synthesis of Heterocycles by a C-C Cross-Coupling/Alkyne-Carbonyl-Metathesis Strategy
    Langer, Peter
    SYNLETT, 2024, : 1965 - 1975
  • [29] Transition-Metal Free C-C Bond Cross-Coupling of Aryl Ethers with Diarylmethanes
    Li, Chenchen
    Qin, Qi
    Guan, Aocong
    Yang, Wen
    Zhao, Wanxiang
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (11): : 7525 - 7534
  • [30] Organocopper cross-coupling reaction for C-C bond formation on highly sterically hindered structures
    Oi, Miku
    Takita, Ryo
    Kanazawa, Junichiro
    Muranaka, Atsuya
    Wang, Chao
    Uchiyama, Masanobu
    CHEMICAL SCIENCE, 2019, 10 (24) : 6107 - 6112