Tetrahydrofuran ring opening and related reactions with an N-heterocyclic carbene-boryl trifluoromethanesulfonate

被引：17
|
作者：
Solovyev, Andrey [2 ]
Lacote, Emmanuel [1 ,3 ]
Curran, Dennis P. [2 ]
机构：
[1] Univ Lyon 1, Inst Chim Lyon, ESCPE Lyon, CNRS,UMR 5265, F-69616 Villeurbanne, France
[2] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
[3] UPMC Univ Paris 06, Inst Parisien Chim Mol, UMR CNRS 7201, F-75005 Paris, France
来源：
DALTON TRANSACTIONS | 2013年 / 42卷 / 03期
基金：
美国国家科学基金会;
关键词：
FRUSTRATED LEWIS PAIRS; CYCLIC ETHERS; BORANE; HYDROGEN; BORON; COMPLEXES; PHOTOPOLYMERIZATIONS; ACTIVATION; RADICALS;
D O I：
10.1039/c2dt31773g
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Reaction of the triflate group in dipp-Imd-BH2OTf with nucleophiles generally occurs by direct substitution to give products dipp-Imd-BH(2)Nu. In contrast, reaction of this boryl triflate with aryloxides (ArO-) in THF resulted in insertion of THF with ring opening in between the NHC-boryl electrophile and the aryloxide to give products dipp-Imd-BH2O(CH2)(4)OAr. The incorporation of THF was observed with other nucleophiles such as ethylthiolate and trimethylsilanolate whose conjugate acids have pK(a) values similar to that of phenol. The cleavage of ethyl acetate and oxetane is reported as well. A possible mechanism is proposed.
引用
下载
收藏
页码：695 / 700
页数：6
相关论文
共 50 条
  • [1] Formation of N-Heterocyclic Carbene-Boryl Radicals through Electrochemical and Photochemical Cleavage of the B-S bond in N-Heterocyclic Carbene-Boryl Sulfides
    Telitel, Sofia
    Vallet, Anne-Laure
    Schweizer, Stephane
    Delpech, Bernard
    Blanchard, Nicolas
    Morlet-Savary, Fabrice
    Graff, Bernadette
    Curran, Dennis P.
    Robert, Marc
    Lacote, Emmanuel
    Lalevee, Jacques
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (45) : 16938 - 16947
  • [2] Facile Synthesis of α-N-Heterocyclic Carbene-Boryl Ketones from N-Heterocyclic Carbene-Boranes and Alkenyl Triflates
    Dai, Wen
    Geib, Steven J.
    Curran, Dennis P.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (31) : 12355 - 12361
  • [3] N-Heterocyclic Carbene Boryl Iodides Catalyze Insertion Reactions of N-Heterocyclic Carbene Boranes and Diazoesters
    Allen, Thomas H.
    Kawamoto, Takuji
    Gardner, Sean
    Geib, Steven J.
    Curran, Dennis P.
    ORGANIC LETTERS, 2017, 19 (13) : 3680 - 3683
  • [4] Generation and Reactions of an Unsubstituted N-Heterocyclic Carbene Boryl Anion
    Monot, Julien
    Solovyev, Andrey
    Bonin-Dubarle, Helene
    Derat, Etienne
    Curran, Dennis P.
    Robert, Marc
    Fensterbank, Louis
    Malacria, Max
    Lacote, Emmanuel
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (48) : 9166 - 9169
  • [5] N-heterocyclic carbene complexes in ring opening polymerization
    Jain, Isha
    Malik, Payal
    EUROPEAN POLYMER JOURNAL, 2021, 150
  • [6] N-Heterocyclic Carbene Stabilized Boryl Radicals
    Valverde, Miguel F. Silva
    Schweyen, Peter
    Gisinger, Daria
    Bannenberg, Thomas
    Freytag, Matthias
    Kleeberg, Christian
    Tamm, Matthias
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (04) : 1135 - 1140
  • [7] Advances in chemistry of N-heterocyclic carbene boryl radicals
    Taniguchi, Tsuyoshi
    CHEMICAL SOCIETY REVIEWS, 2021, 50 (16) : 8995 - 9021
  • [8] N-Heterocyclic Carbene-Mediated Ring Opening of Reduced Diazamagnesacycles
    Obi, Akachukwu D.
    Freeman, Lucas A.
    Dickie, Diane A.
    Gilliard, Robert J., Jr.
    ORGANOMETALLICS, 2020, 39 (24) : 4575 - 4583
  • [9] [3+2]-Dipolar Cycloaddition Reactions of an N-Heterocyclic Carbene Boryl Azide
    Merling, Everett
    Lamm, Vladimir
    Geib, Steven J.
    Lacote, Emmanuel
    Curran, Dennis P.
    ORGANIC LETTERS, 2012, 14 (11) : 2690 - 2693
  • [10] Reactivity and Stability of a Ring-Expanded N-Heterocyclic Carbene Copper(I) Boryl Imidinate
    Charman, Rex S. C.
    Downie, Thomas M. Horsley
    Jerome, Thomas H.
    Mahon, Mary F.
    Liptrot, David J.
    INORGANICS, 2022, 10 (09)
12345