N-Heterocyclic carbene-mediated redox condensation of alcohols

被引:13
|
作者
Kato, Terumasa [1 ]
Matsuoka, Shin-ichi [1 ]
Suzuki, Masato [1 ]
机构
[1] Nagoya Inst Technol, Grad Sch Engn, Dept Life Sci & Appl Chem, Showa Ku, Gokiso Cho, Nagoya, Aichi 4668555, Japan
关键词
TO-TAIL DIMERIZATION; BOND-FORMING REACTIONS; MITSUNOBU REACTION; OXIDATION-REDUCTION; CATALYZED REACTIONS; MICHAEL ACCEPTORS; PHOSPHORIC-ACID; STABLE CARBENE; NHC CATALYSIS; ALKYL-ARYL;
D O I
10.1039/c6cc04154j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
N-Heterocyclic carbenes (NHCs) with a variety of oxidants promote the Mitsunobu-type coupling reactions of alcohols with phenols, carboxylic acids, and phthalimide. Experiments using a chiral alcohol indicate that these reactions proceed via S(N)1 or S(N)2 pathways depending on the polarity of the used solvents. The NHCs are consumed as reducing reagents to form their oxides as readily separable by products.
引用
收藏
页码:8569 / 8572
页数:4
相关论文
共 50 条
  • [1] N-heterocyclic carbene-mediated transformations of silicon reagents
    He, Lin
    Guo, Hao
    Wang, Ying
    Du, Guang-Fen
    Dai, Bin
    TETRAHEDRON LETTERS, 2015, 56 (08) : 972 - 980
  • [2] 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
  • [3] N-Heterocyclic Carbene-Mediated Oxidative Electrosynthesis of Esters in a Microflow Cell
    Green, Robert A.
    Pletcher, Derek
    Leach, Stuart G.
    Brown, Richard C. D.
    ORGANIC LETTERS, 2015, 17 (13) : 3290 - 3293
  • [4] N-Heterocyclic Carbene-Mediated Enantioselective Addition of Phenols to Unsymmetrical Alkylarylketenes
    Concellon, Carmen
    Duguet, Nicolas
    Smith, Andrew D.
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (17) : 3001 - 3009
  • [5] N-Heterocyclic Carbene-Mediated Microfluidic Oxidative Electrosynthesis of Amides from Aldehydes
    Green, Robert A.
    Pletcher, Derek
    Leach, Stuart G.
    Brown, Richard C. D.
    ORGANIC LETTERS, 2016, 18 (05) : 1198 - 1201
  • [6] N-heterocyclic carbene-mediated oxidation of copper(I) in an imidazolium ionic liquid
    Shah, Sameera
    Pietsch, Tobias
    Ruck, Michael
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2023, 78 (3-4): : 105 - 112
  • [7] Kinetic and mechanistic studies of N-heterocyclic carbene-mediated zwitterionic polymerization of cyclic esters
    Shin, Eun Ji
    Jeong, Wonhee
    Culkin, Darcy A.
    Hedrick, James L.
    Waymouth, Robert M.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 237
  • [8] N-Heterocyclic Carbene-Mediated Oxidative Esterification of Aldehydes: Ester Formation and Mechanistic Studies
    Maji, Biswajit
    Vedachalan, Seenuvasan
    Ge, Xin
    Cai, Shuting
    Liu, Xue-Wei
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (09): : 3016 - 3023
  • [9] N-Heterocyclic carbene-mediated zwitterionic polymerization: An expedient organocatalytic route to cyclic polyesters
    Jeong, Wonhee
    Shin, Eun Ji
    Culkin, Darcy A.
    Hedrick, James L.
    Waymouth, Robert M.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 234
  • [10] N-Heterocyclic Carbene-Mediated Carbon-Sulfur Bond-Forming Reactions
    Lv, Jie
    Jin, Zhichao
    Wang, Hongling
    Chi, Yonggui Robin
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2022, 10 (42) : 13901 - 13916