Ring-Opening Carbonyl-Olefin Metathesis of Cyclobutenes

被引：0
|
作者：
Holl, Maxwell G. [1 ]
Lambert, Tristan H. [1 ]
机构：
[1] Cornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USA
来源：
ACS CATALYSIS | 2022年 / 12卷 / 09期
关键词：
carbonyl-olefin metathesis; cyclobutenes; cycloaddition; cycloreversion; hydrazine catalysis;
D O I：
10.1021/acscatal.2c01188
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
The ring-opening carbonyl-olefin metathesis of cyclobutenes to furnish gamma,(5-unsaturated aldehydes-formal Claisen rearrangement products-is reported. The bistrifluoroacetic acid salt of 2,3-diazabicyclo[2.2.2]octane promotes these reactions efficiently with a variety of cyclobutenes and aldehydes, including aliphatic, alpha,fi-unsaturated, aryl, and heteroaryl aldehydes. Catalytic reactions are also demonstrated.
引用
收藏
页码：4813 / 4817
页数：5
相关论文
共 50 条
  • [1] Ring-opening carbonyl-olefin metathesis of norbornenes
    Jermaks, Janis
    Quach, Phong K.
    Seibel, Zara M.
    Pomarole, Julien
    Lambert, Tristan H.
    [J]. CHEMICAL SCIENCE, 2020, 11 (30) : 7884 - 7895
  • [2] GaCl3-Catalyzed Ring-Opening Carbonyl-Olefin Metathesis
    Albright, Haley
    Vonesh, Hannah L.
    Becker, Marc R.
    Alexander, Brandon W.
    Ludwig, Jacob R.
    Wiscons, Ren A.
    Schindler, Corinna S.
    [J]. ORGANIC LETTERS, 2018, 20 (16) : 4954 - 4958
  • [3] Carbonyl-Olefin Metathesis
    Albright, Haley
    Davis, Ashlee J.
    Gomez-Lopez, Jessica L.
    Vonesh, Hannah L.
    Quach, Phong K.
    Lambert, Tristan H.
    Schindler, Corinna S.
    [J]. CHEMICAL REVIEWS, 2021, 121 (15) : 9359 - 9406
  • [4] Catalytic carbonyl-olefin metathesis
    Ludwig, Jacob
    Gianino, Joseph
    Schindler, Corinna
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
  • [5] Catalytic carbonyl-olefin metathesis
    Schindler, Corinna
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [6] Organocatalytic Carbonyl-Olefin Metathesis
    Griffith, Allison K.
    Vanos, Christine M.
    Lambert, Tristan H.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (45) : 18581 - 18584
  • [7] Hydrazine-Catalysed Ring-Opening Metathesis Polymerization Of Cyclobutenes
    Kellner-Rogers, Julian S.
    Hsu, Jesse H.
    Keresztes, Ivan
    Fors, Brett P.
    Lambert, Tristan H.
    [J]. Angewandte Chemie - International Edition, 2024, 63 (52)
  • [8] New catalysts for carbonyl-olefin metathesis
    Davis, Ashlee
    Schindler, Corinna
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
  • [9] New catalysts for carbonyl-olefin metathesis
    Schindler, Corinna
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
  • [10] Carbonyl-olefin metathesis: a key review
    Ravindar, Lekkala
    Lekkala, Revathi
    Rakesh, K. P.
    Asiri, Abdullah M.
    Marwani, Hadi M.
    Qin, Hua-Li
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (08): : 1381 - 1391
12345