Palladium-catalyzed dehydrogenative coupling of terminal alkynes with secondary phosphine oxides

被引:45
作者
Yang, Jia [1 ]
Chen, Tieqiao [1 ]
Zhou, Yongbo [1 ]
Yin, Shuangfeng [1 ]
Han, Li-Biao [1 ,2 ]
机构
[1] Hunan Univ, Coll Chem & Chem Engn, State Key Lab Chemo Biosensing & Chemometr, Changsha 410082, Hunan, Peoples R China
[2] Natl Inst Adv Ind Sci & Technol, Tsukuba, Ibaraki 3058565, Japan
关键词
PHOSPHORUS-BORON BONDS; DIALKYL H-PHOSPHONATES; ONE-POT SYNTHESIS; C-C; COPPER; ALKYNYLPHOSPHONATES; FUNCTIONALIZATION; ACTIVATION; ROUTE; 1-ALKYNYLPHOSPHONATES;
D O I
10.1039/c4cc09567g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The dehydrogenative coupling of terminal alkynes with secondary phosphine oxides is developed. In the presence of a silver additive, palladium acetate could efficiently catalyze the dehydrocoupling of secondary phosphine oxides with a variety of terminal alkynes to produce the corresponding alkynylphosphine oxides in high yields. A reaction mechanism is proposed.
引用
收藏
页码:3549 / 3551
页数:3
相关论文
共 50 条
  • [1] Mechanistic Studies on the Palladium-Catalyzed Cross Dehydrogenative Coupling of P(O)-H Compounds with Terminal Alkynes: Stereochemistry and Reactive Intermediates
    Yang, Jia
    Chen, Tieqiao
    Zhou, Yongbo
    Yin, Shuang-Feng
    Han, Li-Biao
    ORGANOMETALLICS, 2015, 34 (20) : 5095 - 5098
  • [2] Palladium-Catalyzed Denitrogenative Coupling of Aryldiazonium Salts with Terminal Alkynes for the Assembly of Internal Alkynes
    Guo, Ziyang
    Xiong, Xun
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (40)
  • [3] Palladium-Catalyzed Dehydrogenative Coupling of Furans with Styrenes
    Aouf, Chahinez
    Thiery, Emilie
    Le Bras, Jean
    Muzart, Jacques
    ORGANIC LETTERS, 2009, 11 (18) : 4096 - 4099
  • [4] Palladium-Catalyzed Aerobic Oxidative Cross-Coupling Reactions of Terminal Alkynes with Alkylzinc Reagents
    Chen, Mao
    Zheng, Xiaolong
    Li, Wenqing
    He, Jun
    Lei, Aiwen
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (12) : 4101 - +
  • [5] Palladium-catalyzed cross-dehydrogenative-coupling of nitro-substituted internal alkenes with terminal alkenes
    Li, Yunlong
    Liu, Haibo
    Huang, Zilong
    Wang, Hongmei
    Yu, Zhengkun
    TETRAHEDRON LETTERS, 2021, 82
  • [6] LiHMDS-Promoted Palladium-Catalyzed Sonogashira Cross-Coupling of Aryl Fluorides with Terminal Alkynes
    He, Jingjing
    Yang, Kang
    Zhao, Jianhong
    Cao, Song
    ORGANIC LETTERS, 2019, 21 (23) : 9714 - 9718
  • [7] Palladium-Catalyzed branch hydroaminocarbonylation of terminal alkynes with nitroarenes
    Yin, Zhiping
    Yuan, Weiheng
    Liu, Chenwei
    Qin, Xiaowen
    Xu, Tiefeng
    Wu, Xiao-Feng
    JOURNAL OF CATALYSIS, 2024, 439
  • [8] Palladium-Catalyzed Oxidative Cross-Coupling between Heterocycles and Terminal Alkynes with Low Catalyst Loading
    Jie, Xiaoming
    Shang, Yaping
    Hu, Peng
    Su, Weiping
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (13) : 3630 - 3633
  • [9] Palladium-Catalyzed Synthesis of Dibenzophosphole Oxides via Intramolecular Dehydrogenative Cyclization
    Kuninobu, Yoichiro
    Yoshida, Takuya
    Takai, Kazuhiko
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (18) : 7370 - 7376
  • [10] Copper-Catalyzed Cycloaddition between Secondary Phosphine Oxides and Alkynes: Synthesis of Benzophosphole Oxides
    Zhang, Pengbo
    Gao, Yuzhen
    Zhang, Liangliang
    Li, Zhiqiang
    Liu, Yan
    Tang, Guo
    Zhao, Yufen
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (01) : 138 - 142