Base-Promoted Nucleophilic Phosphorylation of Benzyl Fluorides via C(sp3)-F Cleavage

被引:2
|
作者
Sun, Bing-Qian [1 ,2 ]
Yang, Jia [1 ,2 ]
Fan, Lei [1 ,2 ]
Xu, Qian [3 ]
Wang, Shuai [1 ,2 ]
Zhong, Hong [1 ,2 ]
Xiang, Hao-Yue [1 ]
机构
[1] Cent South Univ, Coll Chem & Chem Engn, Changsha 410083, Peoples R China
[2] Cent South Univ, Hunan Prov Key Lab Efficient & Clean Utilizat Mang, Changsha 410083, Peoples R China
[3] Hunan Res Inst Chem Ind, Changsha 410014, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 16期
关键词
F BOND ACTIVATION; CATALYZED ALPHA-ARYLATION; PHOSPHORUS; SUBSTITUTION; DERIVATIVES; EFFICIENT; HALIDES; ROUTE;
D O I
10.1021/acs.joc.4c00098
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, a transition-metal-free phosphorylation of benzyl fluorides with P(O)-H compounds is disclosed. In the presence of t BuOK, various benzyl fluorides react with P(O)-H compounds to produce the corresponding benzyl phosphine oxides, phosphinates, and phosphonates in good to high yields. This base-promoted phosphorylation reaction offers a facile and general strategy for the construction of a C(sp(3))-P bond.
引用
收藏
页码:11739 / 11746
页数:8
相关论文
共 50 条
  • [41] Cu-Catalyzed aerobic oxidative cleavage of C(sp3)-C(sp3) bond: Synthesis of α-ketoamides
    Zhang, Jingming
    Liu, Chengkou
    Yang, Man
    Fang, Zheng
    Guo, Kai
    TETRAHEDRON LETTERS, 2020, 61 (47)
  • [42] Oxidative addition and cleavage of sp3 C-F Bond by pincer iridium complexes
    Choi, Jongwook
    Goldman, Alan S.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
  • [43] Catalytic Formation of C(sp3)-F Bonds via Heterogeneous Photocatalysis
    Tarantino, Giulia
    Hammond, Ceri
    ACS CATALYSIS, 2018, 8 (11): : 10321 - 10330
  • [44] Synthesis of Polycyclic Furan and Chromene Derivatives via Cascade Reactions Enabled by Cleavage of Multiple C(sp3)-F Bonds
    Xie, Ting
    Zhang, Chen
    Zhang, Si-Xuan
    Rao, Weidong
    Xu, Haiyan
    Shen, Zhi-Liang
    Chu, Xue-Qiang
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (21) : 4736 - 4743
  • [45] C(sp3)-C(sp3) Radical-Cross-Coupling Reaction via Photoexcitation
    Patel, Sandeep
    Chakraborty, Arijit
    Chatterjee, Indranil
    ORGANIC LETTERS, 2023, 25 (46) : 8246 - 8251
  • [46] Fe-promoted cross coupling of homobenzylic methyl ethers with Grignard reagents via sp3 C-O bond cleavage
    Luo, Shuang
    Yu, Da-Gang
    Zhu, Ru-Yi
    Wang, Xin
    Wang, Lei
    Shi, Zhang-Jie
    CHEMICAL COMMUNICATIONS, 2013, 49 (71) : 7794 - 7796
  • [47] Palladium-Catalyzed Base-Promoted Arylation of Unactivated C(sp3)-H Bonds by Aryl Iodides: A Practical Approach To Synthesize β-Aryl Carboxylic Acid Derivatives
    Gou, Quan
    Liu, Gang
    Zhou, Lanxiu
    Chen, Suiyun
    Qin, Jun
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (42) : 6314 - 6318
  • [48] Photoredox Polychloroalkylation/Spirocyclization of Activated Alkynes via C(sp3)-H bond Cleavage
    Luo, Zhen-Tao
    Zhong, Long-Jin
    Zhou, Quan
    Xiong, Bi-Quan
    Tang, Ke-Wen
    Liu, Yu
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (06)
  • [49] Unexpected Copper-Catalyzed Aerobic Oxidative Cleavage of C(sp3)-C(sp3) Bond of Glycol Ethers
    Liu, Zhong-Quan
    Zhao, Lixing
    Shang, Xiaojie
    Cui, Zili
    ORGANIC LETTERS, 2012, 14 (12) : 3218 - 3221
  • [50] Selective C(sp3)-C(sp3) Cleavage/Alkynylation of Cycloalkylamides Enables Aminoalkyne Synthesis with Hypervalent Iodine Reagents
    Liu, Zhengyi
    Wu, Shuang
    Chen, Yiyun
    ACS CATALYSIS, 2021, 11 (16) : 10565 - 10573