Photoinduced Homolysis of the Ni-P Bond via Ligand to Metal Charge Transfer for C-P Bond Formation in Nickel Catalysis

被引:8
|
作者
Ma, Yunpeng [1 ]
Luo, Hang [1 ]
Lin, Luqing [1 ]
机构
[1] Dalian Univ Technol, Zhang Dayu Sch Chem, Dalian 116024, Liaoning, Peoples R China
关键词
PHOTOREDOX; PHOSPHORYLATION;
D O I
10.1021/acs.orglett.3c01079
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Photoinduced homolysis of NiII-carbon and -heter-oatom bonds has been well studied for carbon-heteroatom couplings, but homolysis of the NiII-P bond is still undisclosed. Herein, we describe the homolysis of NiII-P bonds via ligand to metal charge transfer to access active nickel(I) complexes and phosphorus-centered radicals under visible-light irradiation for C-P couplings of diaryl phosphine oxides with aryl bromides. Experimental studies demonstrated that visible light enabled homolysis of the NiII-P bond and the NiI/NiIII self-sustained cycle was involved in C-P bond formation. Furthermore, homolysis of the NiII-P bond can be applied to the hydrophosphination of [1.1.1]propellane in single-nickel photocatalysis.
引用
收藏
页码:3492 / 3496
页数:5
相关论文
共 50 条
  • [11] C-P bond formation via selective electrocatalytic C-H phosphorylation
    Khrizanforov, M. N.
    Strekalova, S. O.
    Grinenko, V. V.
    Kononov, A. I.
    Dolengovski, E. L.
    Budnikova, Y. H.
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2019, 194 (4-6) : 384 - 385
  • [12] P-P bond formation via unique metal-ligand cooperation
    Kim, Yeong-Eun
    Lee, Yunho
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [13] Transition Metal-Catalyzed C-P Bond Activation
    Zhang, Fengping
    Luan, Yuxin
    Ye, Mengchun
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (10) : 3880 - 3891
  • [14] Eco-efficient electrocatalytic C-P bond formation
    Budnikova, Yulia H.
    Gryaznova, Tatyana V.
    Grinenko, Valeriya V.
    Dudkina, Yulia B.
    Khrizanforov, Mikhail N.
    PURE AND APPLIED CHEMISTRY, 2017, 89 (03) : 311 - 330
  • [15] Electrosynthesis of Phosphacycles via Dehydrogenative C-P Bond Formation Using DABCO as a Mediator
    Kurimoto, Yuji
    Yamashita, Jun
    Mitsudo, Koichi
    Sato, Eisuke
    Suga, Seiji
    ORGANIC LETTERS, 2021, 23 (08) : 3120 - 3124
  • [16] Transition-Metal-Free C-P Bond Formation via Decarboxylative Phosphorylation of Cinnamic Acids with P(O)H Compounds
    Liu, Lixin
    Zhou, Dan
    Dong, Jianyu
    Zhou, Yongbo
    Yin, Shuang-Feng
    Han, Li-Biao
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (07): : 4190 - 4196
  • [17] Copper Catalyzed C(sp3)- H Bond Alkylation via Photoinduced Ligand-to-Metal Charge Transfer
    Treacy, Sean M.
    Rovis, Tomislav
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (07) : 2729 - 2735
  • [18] Direct Oxidative C-P Bond Formation of Indoles with Dialkyl Phosphites
    Wang, Haolong
    Li, Xincheng
    Wu, Fan
    Wan, Boshun
    SYNTHESIS-STUTTGART, 2012, 44 (06): : 941 - 945
  • [19] Homolytic substitution at phosphorus for C-P bond formation in organic synthesis
    Yorimitsu, Hideki
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 : 1269 - 1277
  • [20] Visible light-mediated C-P bond formation reactions
    Cai, Bao-Gui
    Xuan, Jun
    Xiao, Wen-Jing
    SCIENCE BULLETIN, 2019, 64 (05) : 337 - 350