Palladium-catalyzed C(sp3)-P(III) bond formation reaction with acylphosphines as phosphorus source

被引:6
|
作者
Zhang, Mengyue [1 ]
Ma, Zhichao [1 ]
Du, Hongguang [1 ]
Wang, Zhiqian [1 ]
机构
[1] Beijing Univ Chem Technol, Coll Chem, State Key Lab Chem Resource Engn, Beijing 100029, Peoples R China
基金
中国国家自然科学基金;
关键词
Pd catalyst; Acylphosphine; C(sp(3))-P(III) bond; Alkyl substituted phosphines; P-STEREOGENIC PHOSPHINES; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC ALKYLATION; LIGANDS; PHOSPHORAMIDITES; BORANES; ACID;
D O I
10.1016/j.tetlet.2020.152125
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Palladium-catalyzed C(sp(3))-P(III) bond formation reaction for alkyl substituted phosphines preparation was developed. In this reaction, various alkyl bromides and limited alkyl chlorides reacted with acylphosphine under relative mild and easily accessible condition, and differential phosphines were afforded in good yields. This reaction made up the application of palladium catalysis in C(sp(3))-P(III) bond formation, and indicated a practical application of acylphosphine as a phosphination reagent. (C) 2020 Elsevier Ltd. All rights reserved.
引用
收藏
页数:4
相关论文
共 50 条
  • [1] Palladium-catalyzed C-P(III) bond formation reaction with acylphosphines as phosphorus source
    Yu, Rongrong
    Chen, Xingyu
    Wang, Zhiqian
    TETRAHEDRON LETTERS, 2016, 57 (30) : 3404 - 3406
  • [2] Palladium-Catalyzed C-P(III) Bond Formation by Coupling ArBr/ArOTf with Acylphosphines
    Chen, Xingyu
    Wu, Hongyu
    Yu, Rongrong
    Zhu, Hong
    Wang, Zhiqian
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (13): : 8987 - 8996
  • [3] Palladium-Catalyzed Diacetoxylation of Methylenecyclopropanes via C(SP3)-C(SP3) Bond Breaking
    Jiang, Min
    Shi, Min
    ORGANOMETALLICS, 2009, 28 (19) : 5600 - 5602
  • [4] Palladium(ii)-catalyzed oxidative C(sp3)-P bond formation via C(sp3)-H bond activation
    Chen, Lijin
    Zhou, Zhenfei
    Zhang, Saifei
    Li, Xiaoqian
    Ma, Xuebing
    Dong, Jiaxing
    CHEMICAL COMMUNICATIONS, 2019, 55 (91) : 13693 - 13696
  • [5] Palladium-catalyzed silyl C(sp3)-H bond activation
    Liang, Yun
    Geng, Weizhi
    Wei, Junnian
    Ouyang, Kunbing
    Xi, Zhenfeng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (08) : 1537 - 1542
  • [6] Mechanistic investigation of palladium-catalyzed C(sp3)-N bond formation with DFT methods
    Peacock, D. Matthew
    Jiang, Quan
    Cundari, Thomas
    Hartwig, John
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [7] Palladium-Catalyzed C(sp3)-H Bond Functionalization of Aliphatic Amines
    He, Chuan
    Whitehurst, William G.
    Gaunt, Matthew J.
    CHEM, 2019, 5 (05): : 1031 - 1058
  • [8] Palladium-Catalyzed Nitrile-Assisted C(sp3)-Cl Bond Formation for Synthesis of Dichlorides
    He, Dandan
    Huang, Liangbin
    Li, Jianxiao
    Wu, Wanqing
    Jiang, Huanfeng
    ORGANIC LETTERS, 2019, 21 (20) : 8308 - 8311
  • [9] Palladium-catalyzed remote internal C(sp3)-H bond chlorination of alkenes
    Wang, Yao-Xin
    Wang, Zhen
    Yang, Xiao-Hui
    NATURE COMMUNICATIONS, 2024, 15 (01)
  • [10] Palladium-Catalyzed Decarboxylative Alkynylation of α-Acyloxyketones by C(sp3)-O Bond Cleavage
    Doi, Ryohei
    Yabuta, Akimasa
    Sato, Yoshihiro
    CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (23) : 5884 - 5888