Redox-Neutral Generation of Iminyl Radicals by N-Heterocyclic Carbene Catalysis: Rapid Access to Phenanthridines from Vinyl Azides

被引：0
|
作者：
Liu, Lixia [1 ]
Zhang, Qijing [1 ]
Wang, Chengming [1 ]
机构：
[1] Jinan Univ, Coll Chem & Mat Sci, Guangdong Prov Key Lab Funct Supramol Coordinat Ma, Guangzhou 511443, Guangdong, Peoples R China
来源：
ORGANIC LETTERS | 2022年
关键词：
CYCLIZATION;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An N-heterocyclic carbene-catalyzed oxidant-, metal-and light-free iminyl radical generation pathway stemming from the reaction of vinyl azide and alpha-bromo ester is uncovered. This newly developed methodology is successfully applied to the redox-neutral construction of a number of diversified phenanthridine derivatives with nice functional group compatibility. Insights from the mechanism study reveal that this NHC-catalyzed transformation potentially proceeds through an alkyl radical addition-initiated HAS process, with the iminyl radical as an active intermediate.
引用
收藏
页数：5
相关论文
共 50 条
  • [31] Divergent Reactivity of Iminyl Radicals in Four Interrupted Pathways for the Synthesis of Cyclic/Acyclic Ketones and N-Heterocycles from Vinyl Azides and Phenylacetic Acids
    Paul, Swagota
    Baruah, Ashitosh
    More, Atul A.
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (18): : 13128 - 13136
  • [32] On the Role of N-Heterocyclic Carbene Salts in Alkyl Radical Generation from Alkyl Alcohols: A Computational Study
    Sanosa, Nil
    Ambrosi, Diego
    Ruiz-Campos, Pedro
    Sampedro, Diego
    Funes-Ardoiz, Ignacio
    CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (40)
  • [33] Electron Paramagnetic Resonance and Computational Studies of Radicals Derived from Boron-Substituted N-Heterocyclic Carbene Boranes
    Walton, John C.
    Brahmi, Malika Makhlouf
    Monot, Julien
    Fensterbank, Louis
    Malacria, Max
    Curran, Dennis P.
    Lacote, Emmanuel
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (26) : 10312 - 10321
  • [34] Access to Gold(I) Protic N-Heterocyclic Carbene Complexes from Trinuclear Gold(I) Imidazolate Clusters
    Ruiz, Javier
    Mateo, Maria A.
    ORGANOMETALLICS, 2021, 40 (10) : 1515 - 1522
  • [35] New chiral N-heterocyclic carbene complexes derived from amino acids: Versatile ligands for asymmetric aqueous catalysis
    Faul, Stefan Holger
    Schlichtiger, Alice
    Eppinger, Jorg
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 239
  • [36] Photoinduced Electron Transfer from Xanthates to Acyl Azoliums: Divergent Ketone Synthesis via N-Heterocyclic Carbene Catalysis
    Tan, Chang-Yin
    Kim, Minseok
    Hong, Sungwoo
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (32)
  • [37] A Second-Generation Palladacycle Architecture Bearing a N-Heterocyclic Carbene and Its Catalytic Behavior in Buchwald-Hartwig Amination Catalysis
    Ostrowska, Sylwia
    Palio, Lorenzo
    Czapik, Agnieszka
    Bhandary, Subhrajyoti
    Kwit, Marcin
    Van Hecke, Kristof
    Nolan, Steven P.
    CATALYSTS, 2023, 13 (03)
  • [38] Air-/Heat-Stable Crystalline Carbon-Centered Radicals Derived from an Annelated N-Heterocyclic Carbene
    Zhao, Jing
    Li, Xin
    Han, Ying-Feng
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (36) : 14428 - 14432
  • [39] Expedient Access to Normal- and Abnormal- N-Heterocyclic Carbene (NHC) Magnesium Compounds from Imidazolium Salts
    Ghadwal, Rajendra S.
    Rottschaefer, Dennis
    Schuermann, Christian J.
    ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 2016, 642 (22): : 1236 - 1240
  • [40] Micellar N-Heterocyclic Carbene-like Organic Catalysis from Polymeric Nanoreactors Immobilizing Benzimidazolium Acetate Motifs in Their Core
    Wirotius, Anne-Laure
    Lambert, Romain
    Darde, Thomas
    Harrisson, Simon
    Taton, Daniel
    ACS CATALYSIS, 2024, 14 (13): : 10271 - 10279
12345