Synthesis of 2-Boryl Allylboronates by a Bimetallic Platinum/Zinc-Promoted Diborylation of Propargylic Amines

被引:0
|
作者
Shi, Xiao-Nan [1 ,2 ]
Wang, Jia-Le [1 ,2 ]
Wu, Jiang-Bin [1 ,2 ]
Zhuo, Chun-Xiang [1 ,2 ,3 ]
机构
[1] Xiamen Univ, State Key Lab Phys Chem Solid Surfaces, Key Lab Chem Biol Fujian Prov, Xiamen 361005, Peoples R China
[2] Xiamen Univ, Coll Chem & Chem Engn, Xiamen 361005, Peoples R China
[3] Xiamen Univ, Shenzhen Res Inst, Shenzhen 518057, Peoples R China
基金
中国国家自然科学基金;
关键词
2-boryl allylboronates; propargylic amines; platinum catalysis; bimetallic synergistic effect; diborylation; ALDEHYDE-ALKYNE-AMINE; DIBORATION; ALLENES; ALLYL;
D O I
10.1055/a-2030-6797
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2-Boryl allylboronates, which contain both a C(sp(2))-B bond and a C(sp(3))-B bond, are attractive synthetic intermediates due to their diverse reactivity profiles toward a wide range of organic transformations. We report a facile approach to (Z)-2-boryl allylboronates through a Pt/Zn-promoted diborylation reaction of readily available propargylic amines. An array of valuable (Z)-2-boryl allylboronates were obtained in up to 73% yield in the presence of 2.5 mol% of Pt(PPh3)(4) and 50 mol% of ZnBr2.
引用
收藏
页码:1573 / 1576
页数:4
相关论文
共 6 条
  • [1] Synthesis of Vinyl-, Allyl-, and 2-Boryl Allylboronates via a Highly Selective Copper-Catalyzed Borylation of Propargylic Alcohols
    Mao, Lujia
    Bertermann, Ruediger
    Emmert, Katharina
    Szabo, Kalman J.
    Marder, Todd B.
    ORGANIC LETTERS, 2017, 19 (24) : 6586 - 6589
  • [2] Zinc diiodide-promoted synthesis of trisubstituted allenes from propargylic amines
    Kuang, Jinqiang
    Tang, Xinjun
    Ma, Shengming
    ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (05): : 470 - 475
  • [3] Copper/DTBP-Promoted Oxyselenation of Propargylic Amines with Diselenides and CO2: Synthesis of Selenyl 2-Oxazolidinones
    Chen, Jia-Min
    Qi, Lin
    Zhang, Linlin
    Li, Li-Jun
    Hou, Cong-Ying
    Li, Wei
    Wang, Li-Jing
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (16): : 10924 - 10933
  • [4] Zinc-promoted cyclization of tosylhydrazones and 2-(dimethylamino)malononitrile: an efficient strategy for the synthesis of substituted 1-tosyl-1H-pyrazoles
    Zhang, Bang-Hong
    Lei, Lin-Sheng
    Liu, Si-Zhan
    Mou, Xue-Qing
    Liu, Wei-Ting
    Wang, Shao-Hua
    Wang, Jie
    Bao, Wen
    Zhang, Kun
    CHEMICAL COMMUNICATIONS, 2017, 53 (61) : 8545 - 8548
  • [5] AN EFFICIENT SYNTHESIS OF 3-CHLOROHOMOALLYL ALCOHOLS - ZINC-PROMOTED 2-CHLOROALLYLATION OF CARBONYL-COMPOUNDS WITH 2,3-DICHLOROPROPENE IN AN AQUEOUS SOLVENT SYSTEM
    ODA, Y
    MATSUO, S
    SAITO, K
    TETRAHEDRON LETTERS, 1992, 33 (01) : 97 - 100
  • [6] A NEW, ZINC-PROMOTED SYNTHESIS OF 1,4-(1,5)-ANHYDRO-2-DEOXY-PENT-(HEX)-1-ENITOLS (FURANOID AND PYRANOID GLYCALS)
    CSUK, R
    FURSTNER, A
    GLANZER, BI
    WEIDMANN, H
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (15) : 1149 - 1150