One-Pot Transformation of Aldehydes to Ketones via Minisci-Type Reaction of Imines

被引:8
|
作者
Rubanov, Zakhar M. [1 ]
Levin, Vitalij V. [1 ]
Dilman, Alexander D. [1 ]
机构
[1] ND Zelinskii Inst Organ Chem, Moscow 119991, Russia
关键词
C(SP(2))-H FUNCTIONALIZATION; RADICAL-ADDITION; BOND;
D O I
10.1021/acs.orglett.3c03764
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A method for the conversion of aldehydes to ketones via the preliminary formation of aldiminines is described. The imines are involved in acid promoted Minisci-type reaction with alkyl radicals generated from esters of N-hydroxylphthalimide under photoredox conditions. Aminyl radical cations formed after the addition of the iminium ions are believed to be key intermediates, which determine the reaction outcome.
引用
收藏
页码:8751 / 8755
页数:5
相关论文
共 50 条
  • [31] One-pot preparation of ternary and quaternary iminium salts from aldehydes and ketones
    Saba, Shahrokh
    Vrkic, Diane
    Cascella, Clair
    DaSilva, Ida
    Carta, Kristine
    Kojtari, Adeline
    JOURNAL OF CHEMICAL RESEARCH, 2008, (06) : 301 - 304
  • [33] Efficient Synthesis of Dicycloalkenopyridines: One-pot Multicomponent Condensation of Aldehydes with Cyclic Ketones
    Cai Xi-mei
    Wang Qi-fang
    Yan Chao-guo
    CHEMICAL RESEARCH IN CHINESE UNIVERSITIES, 2009, 25 (05) : 657 - 661
  • [34] A SIMPLE ONE-POT PROCEDURE FOR SYNTHESIS OF CERTAIN SUBSTITUTED THIOPHENE ALDEHYDES AND KETONES
    MICHAEL, U
    GRONOWIT.S
    ACTA CHEMICA SCANDINAVICA, 1968, 22 (04): : 1353 - &
  • [35] Regiospecific Benzoylation of Electron-Deficient N-Heterocycles with Methylbenzenes via a Minisci-Type Reaction
    Ali, Wajid
    Behera, Ahalya
    Guin, Srimanta
    Patel, Bhisma K.
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (11): : 5625 - 5632
  • [36] Visible-Light-Mediated Trifluoroalkylation of Isoquinolines via Three-Component Minisci-Type Reaction
    Thakur, Ankita
    Gupta, Shiv Shankar
    Sharma, Upendra
    ORGANIC LETTERS, 2024, 26 (40) : 8515 - 8520
  • [37] Synthesis of Benzimidazolones via One-Pot Reaction of Hydroxylamines, Aldehydes, and Trimethylsilyl Cyanide Promoted by Diacetoxyiodobenzene
    Zhang, Huaiyuan
    Huang, Danfeng
    Wang, Ke-Hu
    Li, Jun
    Su, Yingpeng
    Hu, Yulai
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (03): : 1600 - 1609
  • [38] One-Pot Multicomponent Synthesis of β-Lactams via In Situ Generated Imines
    Mozaffari, Abolfazl
    Jarrahpour, Aliasghar
    Alborz, Maryam
    Turos, Edward
    CHEMISTRYSELECT, 2019, 4 (19): : 5950 - 5953
  • [39] Practical one-pot preparation of ketones from aryl and alkyl bromides with aldehydes and DIH via Grignard reagents
    Dohi, Souya
    Moriyama, Katsuhiko
    Togo, Hideo
    TETRAHEDRON, 2012, 68 (32) : 6557 - 6564
  • [40] Synthesis of enol phosphates directly from ketones via a modified one-pot Perkow reaction
    Guo, Huichuang
    Zhang, Yulong
    Li, Zhenya
    Zhao, Peichao
    Li, Ning
    Shi, Enxue
    RSC ADVANCES, 2022, 12 (23) : 14844 - 14848