One-Pot Hydroxy Group Activation/Carbon-Carbon Bond Forming Sequence Using a Bronsted Base/Bronsted Acid System

被引：40
|
作者：
Devineau, Alice [1 ]
Pousse, Guillaume [2 ]
Taillier, Catherine [1 ]
Blanchet, Jerome [2 ]
Rouden, Jacques [2 ]
Dalla, Vincent [1 ]
机构：
[1] Univ Havre, URCOM, EA 3221, FR3038, F-76058 Le Havre, France
[2] Univ Caen Basse Normandie, ENSICAEN, Lab Chim Mol & Thioorgan, UMR 6507,CNRS,INC3M,FR3038, F-14050 Caen, France
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2010年 / 352卷 / 17期
关键词：
N-acyliminium; alkylation; electrophilic alcohols; sequential organocatalysis; trichloroacetimidates; NUCLEOPHILIC-SUBSTITUTION REACTIONS; ACYLIMINIUM ION CHEMISTRY; SITE-ISOLATED BASE; ALPHA-AMIDOALKYLATION; HIGHLY EFFICIENT; CATALYSTS; ALCOHOLS; TRIFLATE; ACETATES;
D O I：
10.1002/adsc.201000602
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A new sequential two-step multicatalytic strategy is presented consisting in the efficient DBU-catalysed trichloroacetimidation of an alcohol followed by a ditriflylamine (Tf2NH)-catalysed intermolecular alkylation by silicon-based nucleophiles and C-H nucleophiles. The distinct feature of the trichloroacetimidate group allows use of weaker acid catalysts such as 1,1'-bi-2-naphthol (BINOL)-derived phosphoric acid, pointing out the possible development of an enantioselective variant. This unprecedented sequential one-pot Bronsted base-Bronsted acid catalysis further expands the synthetic scope of the trichloroacetimidate group.
引用
收藏
页码：2881 / 2886
页数：6
相关论文
共 50 条
  • [21] Synthesis of 3,3-disubstituted oxindoles by one-pot integrated Bronsted base-catalyzed trichloroacetimidation of 3-hydroxyoxindoles and Bronsted acid-catalyzed nucleophilic substitution reaction
    Piemontesi, Cyril
    Wang, Qian
    Zhu, Jieping
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (09) : 1533 - 1536
  • [22] LEWIS ACID-MEDIATED CARBON-CARBON BOND FORMING REACTION USING THE PUMMERER REARRANGEMENT PRODUCTS FROM CHIRAL BETA-HYDROXY SULFOXIDES
    KOSUGI, H
    WATANABE, Y
    UDA, H
    CHEMISTRY LETTERS, 1989, (10) : 1865 - 1868
  • [23] One-Pot Conversion of Carbohydrates into 5-(Hydroxymethyl)furfural using Heterogeneous Lewis-Acid and Bronsted-Acid Catalysts
    Zhang, Tingwei
    Fan, Wei
    Li, Wenzhi
    Xu, Zhiping
    Xin, Haosheng
    Su, Mingxue
    Lu, Yijuan
    Ma, Longlong
    ENERGY TECHNOLOGY, 2017, 5 (05) : 747 - 755
  • [24] Bronsted Acid-Mediated Domino One-Pot Dual C-C Bond Formation: Chemoselective Synthesis of Fused Tricyclic Ketones
    Niharika, Pedireddi
    Ramulu, Bokka Venkat
    Satyanarayana, Gedu
    ACS OMEGA, 2018, 3 (01): : 218 - 228
  • [25] One-pot synthesis of polycyclic ring systems via titanium-mediated carbon-carbon bond formation. Activation of cyclopentadienyl ligand via irreversible reductive elimination
    Vu, AT
    Crowe, WE
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 212 : 11 - ORGN
  • [26] Coupling of hybrid electrophores through a one-pot process involving six electron transfers, four C-H bond activations and one carbon-carbon double bond formation
    Miyazaki, Akira
    Ogyu, Yoshiyuki
    Justaud, Frederic
    Ouahab, Lahcene
    Halet, Jean-Francois
    Costuas, Karine
    Gendron, Frederic
    Lapinte, Claude
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
  • [27] Acid-base bifunctional catalysis of silica-alumina-supported organic amines for carbon-carbon bond-forming reactions
    Motokura, Ken
    Tomita, Mitsuru
    Tada, Mizuki
    Iwasawa, Yasuhiro
    CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (13) : 4017 - 4027
  • [28] Bronsted Acid Mediated (sp3)Carbon-Fluorine Bond Activation: Inter- and Intramolecular Arylation of Trifluoromethylated Arenes
    Wang Fei
    Hu Jinbo
    CHINESE JOURNAL OF CHEMISTRY, 2009, 27 (01) : 93 - 98
  • [29] One-pot copolymerization of epoxides/carbon dioxide and lactide using a ternary catalyst system
    Li, Xiang
    Hu, Chenyang
    Pang, Xuan
    Duan, Ranlong
    Chen, Xuesi
    CATALYSIS SCIENCE & TECHNOLOGY, 2018, 8 (24) : 6452 - 6457
  • [30] SAFE ONE-POT CARBON-CARBON BOND FORMATION WITH LITHIATED NITROSAMINES INCLUDING DENITROSATION BY SEQUENTIAL REDUCTION WITH LITHIUM ALUMINUM-HYDRIDE AND RANEY-NICKEL
    SEEBACH, D
    WYKYPIEL, W
    SYNTHESIS-STUTTGART, 1979, (06): : 423 - 424
12345