An air-stable radical with a redox-chameleonic amide

被引:7
|
作者
Peltier, Jesse L. [1 ]
Serrato, Melinda R. [1 ]
Thery, Valentin [2 ]
Pecaut, Jacques [3 ]
Tomas-Mendivil, Eder [2 ]
Bertrand, Guy [1 ]
Jazzar, Rodolphe [1 ]
Martin, David [2 ]
机构
[1] Univ Calif San Diego, Dept Chem & Biochem, UCSD CNRS Joint Res Chem Lab IRL 3555, La Jolla, CA 92093 USA
[2] Univ Grenoble Alpes, DCM, CNRS, F-38000 Grenoble, France
[3] Univ Grenoble Alpes, INAC SyMMES, CNRS, CEA,UMR 5819, F-38000 Grenoble, France
关键词
SELECTIVE PHOTOCYCLIZATION; AMINO-ACIDS; CARBENES; STABILITY; 2-QUINUCLIDONIUM; REACTIVITY; COMPLEXES; OXIDATION; METALS; CATION;
D O I
10.1039/d2cc05404c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An air-stable (amino)(amido)radical was synthesized by reacting a cyclic (alkyl)(amino)carbene with carbazoyl chloride, followed by one-electron reduction. We show that an adjacent radical center weakens the amide bond. It enables the amino group to act as a strong acceptor under steric contraint, thus enhancing the stabilizing capto-dative effect.
引用
收藏
页码:595 / 598
页数:4
相关论文
共 50 条
  • [1] An air-stable radical with a redox-chameleonic amide
    Peltier, Jesse L.
    Serrato, Melinda R.
    Thery, Valentin
    Pecaut, Jacques
    Tomás-Mendivil, Eder
    Bertrand, Guy
    Jazzar, Rodolphe
    Martin, David
    Chemical Communications, 2022, 59 (05): : 595 - 598
  • [2] An Air-Stable Oxyallyl Radical Cation
    Martin, David
    Moore, Curtis E.
    Rheingold, Arnold L.
    Bertrand, Guy
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (27) : 7014 - 7017
  • [3] A remarkably air-stable quinodimethane radical cation
    Harada, Mei
    Tanioka, Masaru
    Muranaka, Atsuya
    Aoyama, Tetsuya
    Kamino, Shinichiro
    Uchiyama, Masanobu
    CHEMICAL COMMUNICATIONS, 2020, 56 (66) : 9565 - 9568
  • [4] An Air-Stable, Neutral Phenothiazinyl Radical with Substantial Radical Stabilization Energy
    Sigmund, Lukas M.
    Ebner, Fabian
    Joest, Christoph
    Spengler, Jonas
    Goennheimer, Nils
    Hartmann, Deborah
    Greb, Lutz
    CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (14) : 3152 - 3156
  • [5] An air-stable Ni(III) complex with thiolate, phenolate and amide ligation
    Tripathi, A
    Syal, RK
    Bharadwaj, PK
    POLYHEDRON, 1999, 18 (17) : 2229 - 2232
  • [6] Air-stable redox-active nanomagnets with lanthanide spins radical-bridged by a metal–metal bond
    Fupin Liu
    Georgios Velkos
    Denis S. Krylov
    Lukas Spree
    Michal Zalibera
    Rajyavardhan Ray
    Nataliya A. Samoylova
    Chia-Hsiang Chen
    Marco Rosenkranz
    Sandra Schiemenz
    Frank Ziegs
    Konstantin Nenkov
    Aram Kostanyan
    Thomas Greber
    Anja U. B. Wolter
    Manuel Richter
    Bernd Büchner
    Stanislav M. Avdoshenko
    Alexey A. Popov
    Nature Communications, 10
  • [7] An Air-Stable Alkene-Derived Organic Radical Cation
    Kumar, Rahul
    Chandra, Shubhadeep
    Nayak, Mithilesh Kumar
    Hazari, Arijit Singha
    Elvers, Benedict J.
    Schulzke, Carola
    Sarkar, Biprajit
    Jana, Anukul
    ACS OMEGA, 2022, 7 (01): : 837 - 843
  • [8] Amide bond formation using an air-stable source of AlMe3
    Novak, Andrew
    Humphreys, Luke D.
    Walker, Matthew D.
    Woodward, Simon
    TETRAHEDRON LETTERS, 2006, 47 (32) : 5767 - 5769
  • [9] Air-Stable Membrane-Free Magnesium Redox Flow Batteries
    Gautam, Rajeev K.
    McGrath, Jack J.
    Wang, Xiao
    Jiang, Jianbing Jimmy
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (41) : 28414 - 28426
  • [10] Air-stable redox-active nanomagnets with lanthanide spins radical-bridged by a metal-metal bond
    Liu, Fupin
    Velkos, Georgios
    Krylov, Denis S.
    Spree, Lukas
    Zalibera, Michal
    Ray, Rajyavardhan
    Samoylova, Nataliya A.
    Chen, Chia-Hsiang
    Rosenkranz, Marco
    Schiemenz, Sandra
    Ziegs, Frank
    Nenkov, Konstantin
    Kostanyan, Aram
    Greber, Thomas
    Wolter, Anja U. B.
    Richter, Manuel
    Buechner, Bernd
    Avdoshenko, Stanislav M.
    Popov, Alexey A.
    NATURE COMMUNICATIONS, 2019, 10 (1)