Metal-free ring-opening of epoxides with potassium trifluoroborates

被引:24
|
作者
Roscales, Silvia [1 ]
Csaky, Aurelio G. [1 ]
机构
[1] Univ Complutense, Inst Pluridisciplinar, E-28040 Madrid, Spain
关键词
CONJUGATE ADDITION; STEREOSELECTIVE-SYNTHESIS; ALKENYLBORONIC ACIDS; BORONIC ACIDS; 1,4-ADDITION; KETONES;
D O I
10.1039/c3cc47360k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The ring-opening of epoxides with potassium trifluoroborates proceeds smoothly in the presence of trifluoroacetic anhydride under metal-free conditions. The reactions are regioselective and afford a single diastereomer. Both electron-rich and electron-poor aryltrifluoroborates are tolerated.
引用
收藏
页码:454 / 456
页数:3
相关论文
共 50 条
  • [21] Comparison of Pyrylium and Thiopyrylium Photooxidants in Metal-Free Ring-Opening Metathesis Polymerization
    Pascual, Laura M. M.
    Dunford, Damian G.
    Goetz, Adam E.
    Ogawa, Kelli A.
    Boydston, Andrew J.
    SYNLETT, 2016, 27 (05) : 759 - 762
  • [22] Metal-free ring-opening polymerization of glycidyl phenyl ether by tetrabutylammonium fluoride
    Morinaga, Hisatoyo
    Ochiai, Bungo
    Endo, Takeshi
    MACROMOLECULES, 2007, 40 (16) : 6014 - 6016
  • [23] Implementation of metal-free ring-opening polymerization in the preparation of aliphatic polycarbonate materials
    Mespouille, Laetitia
    Coulembier, Olivier
    Kawalec, Michal
    Dove, Andrew P.
    Dubois, Philippe
    PROGRESS IN POLYMER SCIENCE, 2014, 39 (06) : 1144 - 1164
  • [24] POTASSIUM DIHYDROGEN TRIFLUORIDE - A NOVEL FLUORINATING REAGENT FOR RING-OPENING OF EPOXIDES
    TAMURA, M
    SHIBAKAMI, M
    ARIMURA, T
    KUROSAWA, S
    SEKIYA, A
    JOURNAL OF FLUORINE CHEMISTRY, 1995, 70 (01) : 1 - 3
  • [25] Non-metal with metal behavior: metal-free coordination-insertion ring-opening polymerization
    Wang, Xin
    Xu, Jiaxi
    Li, Zhenjiang
    Liu, Jingjing
    Sun, Jie
    Hadjichristidis, Nikos
    Guo, Kai
    CHEMICAL SCIENCE, 2021, 12 (32) : 10732 - 10741
  • [26] Regioselective ring-opening of epoxides towards Markovnikov alcohols: a metal-free catalytic approach using abnormal N-heterocyclic carbene
    Sreejyothi, P.
    Sarkar, Pallavi
    Dutta, Supriti
    Das, Arpan
    Pati, Swapan K.
    Mandal, Swadhin K.
    CHEMICAL COMMUNICATIONS, 2022, 58 (68) : 9540 - 9543
  • [27] Fully alternating and regioselective ring-opening copolymerization of phthalic anhydride with epoxides using highly active metal-free Lewis pairs as a catalyst
    Kummari, Anjaneyulu
    Pappuru, Sreenath
    Chakraborty, Debashis
    POLYMER CHEMISTRY, 2018, 9 (29) : 4052 - 4062
  • [28] Mechanochemical Ring-Opening of Allylic Epoxides
    Barbee, Meredith H.
    Wang, Junpeng
    Kouznetsova, Tatiana
    Lu, Meilin
    Craig, Stephen L.
    MACROMOLECULES, 2019, 52 (16) : 6234 - 6240
  • [29] RING-OPENING REACTIONS OF DELTACYCLENE EPOXIDES
    LAUTENS, M
    CRUDDEN, CM
    TETRAHEDRON LETTERS, 1989, 30 (36) : 4803 - 4806
  • [30] Expanded Functionality of Polymers Prepared Using Metal-Free Ring-Opening Metathesis Polymerization
    Goetz, Adam E.
    Pascual, Laura M. M.
    Dunford, Damian G.
    Ogawa, Kelli A.
    Knorr, Daniel B., Jr.
    Boydston, Andrew J.
    ACS MACRO LETTERS, 2016, 5 (05): : 579 - 582