Diversified Synthesis of All-Carbon Quaternary gem-Difluorinated Cyclopropanes via Copper-Catalyzed Cross-Coupling

被引：13
|
作者：
Li, Bin [1 ,2 ,3 ]
Shi, Jiang-Ling [1 ,2 ,3 ]
Xia, Ying [1 ,2 ,3 ]
机构：
[1] Sichuan Univ, West China Sch Publ Hlth, Chengdu 610041, Peoples R China
[2] Sichuan Univ, West China Hosp 4, Chengdu 610041, Peoples R China
[3] Sichuan Univ, State Key Lab Biotherapy, Chengdu 610041, Peoples R China
来源：
ORGANIC LETTERS | 2023年 / 25卷 / 15期
关键词：
CYCLOADDITION; ALKYNES;
D O I：
10.1021/acs.orglett.3c00751
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The construction of all-carbon quaternary centers in small-ring systems is important but challenging in organic synthesis. Herein, by taking gem-difluorocyclopropyl bromides (DFCBs) as a type of general and versatile building block, we developed a practical method for building all-carbon quaternary centers in gem-difluorinated cyclopropanes (DFCs). The reaction relies on the involvement of a gem-difluorocyclopropyl radical intermediate, which can couple with a wide range of nucleophiles under copper catalysis.
引用
收藏
页码：2674 / 2679
页数：6
相关论文
共 50 条
  • [1] Enantioselective Formation of All-Carbon Quaternary Stereocenters in gem-Difluorinated Cyclopropanes via Rhodium-Catalyzed Stereoablative Kinetic Resolution
    Jiang, Zhong-Tao
    Chen, Zhengzhao
    Zeng, Yaxin
    Shi, Jiang-Ling
    Xia, Ying
    ORGANIC LETTERS, 2022, 24 (33) : 6176 - 6181
  • [2] Synthesis of gem-Difluorinated Isoxazoles via Palladium-Catalyzed Oxylallylation of Alkynone Oxime Ethers
    Li, Jianxiao
    Hong, Chenjing
    Niu, Yanan
    Wang, Bowen
    Xiong, Wenfang
    Jiang, Huanfeng
    CHEMISTRY-AN ASIAN JOURNAL, 2023, 18 (18)
  • [3] Copper-Catalyzed Oxidative Cross-Coupling of Sulfoximines and Alkynes
    Wang, Long
    Huang, He
    Priebbenow, Daniel L.
    Pan, Fang-Fang
    Bolm, Carsten
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (12) : 3478 - 3480
  • [4] Oxidative Aminoarylselenation of Maleimides via Copper-Catalyzed Four-Component Cross-Coupling
    Gao, Xue
    Tang, Liyang
    Huang, Lehao
    Huang, Zu-Sheng
    Ma, Yunfei
    Wu, Ge
    ORGANIC LETTERS, 2019, 21 (03) : 745 - 748
  • [5] Copper-catalyzed cross-coupling reactions of bromoalkynols with terminal alkynes in supercritical carbon dioxide
    Jiang, Huan-Feng
    Wang, A-Zhong
    SYNTHESIS-STUTTGART, 2007, (11): : 1649 - 1654
  • [6] A convenient and direct route to phosphinoalkynes via copper-catalyzed cross-coupling of terminal alkynes with chlorophosphanes
    Afanasiev, VV
    Beletskaya, IP
    Kazankova, MA
    Efimova, IV
    Antipin, MU
    SYNTHESIS-STUTTGART, 2003, (18): : 2835 - 2838
  • [7] Efficient Copper-Catalyzed Cross-Coupling Reaction of Alkynes with Aryl Iodides
    Lin, Che-Hung
    Wang, Yu-Jen
    Lee, Chin-Fa
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (23) : 4368 - 4371
  • [8] The synthesis of arylcyanamides: a copper-catalyzed consecutive desulfurization and C-N cross-coupling strategy
    Boddapati, S. N. Murthy
    Polam, Naresh
    Mutchu, Baby Ramana
    Bollikolla, Hari Babu
    NEW JOURNAL OF CHEMISTRY, 2018, 42 (02) : 918 - 922
  • [9] Copper-Catalyzed Asymmetric Propargylic Alkylation with Oxindoles: Diastereo- and Enantioselective Construction of Vicinal Tertiary and All-Carbon Quaternary Stereocenters
    Xia, Jin-Tao
    Hu, Xiang-Ping
    ORGANIC LETTERS, 2020, 22 (03) : 1102 - 1107
  • [10] Transmetalation of Alkylzirconocenes in Copper-Catalyzed Alkyl-Alkynyl Cross-Coupling Reactions
    Indukuri, Kiran
    Riant, Olivier
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (14) : 2425 - 2433
12345