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
  • [1] Borylation of azines via a Minisci-type reaction
    Yang, Shengbiao
    Ye, Juntao
    CHEM, 2021, 7 (07): : 1703 - 1705
  • [2] Tandem vinyl radical Minisci-type annulation on pyridines: one-pot expeditious access to azaindenones
    Xia, Dong
    Duan, Xin-Fang
    CHEMICAL COMMUNICATIONS, 2021, 57 (99) : 13570 - 13573
  • [3] One-Pot Multicomponent Condensation Reaction of Aldehydes with Cyclic Ketones
    Wu, Ping
    Cai, Xi-Mei
    Wang, Qi-Fang
    Yan, Chao-Guo
    SYNTHETIC COMMUNICATIONS, 2011, 41 (06) : 841 - 850
  • [4] A ONE-POT REDUCTIVE ACETYLATION OF ALDEHYDES AND KETONES
    RAO, BR
    NAMBUDIRY, MEN
    SYNTHETIC COMMUNICATIONS, 1991, 21 (17) : 1721 - 1727
  • [5] Acids to aldehydes in one-pot reaction
    不详
    CHEMICAL & ENGINEERING NEWS, 1998, 76 (46) : 30 - 30
  • [6] Reductive heterocyclizations via indium/iodine-promoted one-pot conversion of 2-nitroaryl aldehydes, ketones, and imines
    Han, Rongbi
    Son, Kee In
    Ahn, Gil Hwan
    Jun, Young Moo
    Lee, Byung Min
    Park, Younbong
    Kim, Byeong Hyo
    TETRAHEDRON LETTERS, 2006, 47 (41) : 7295 - 7299
  • [7] Simple One-pot Conversion of Aldehydes and Ketones to Enals
    Valenta, Petr
    Drucker, Natalie A.
    Bode, Jeffrey W.
    Walsh, Patrick J.
    ORGANIC LETTERS, 2009, 11 (10) : 2117 - 2119
  • [8] A Chemoselective, One-Pot Transformation of Aldehydes to Nitriles
    Laulhe, Sebastien
    Gori, Sadakatali S.
    Nantz, Michael H.
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (20): : 9334 - 9337
  • [9] Photocatalytic One-Pot Synthesis of Homoallyl Ketones via a Norrish Type I Reaction of Cyclopentanones
    Okada, Megumi
    Yamada, Keiichi
    Fukuyama, Takahide
    Ravelli, Davide
    Fagnoni, Maurizio
    Ryu, Ilhyong
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (18): : 9365 - 9369
  • [10] A mild one-pot transformation of nitroalkanes to ketones or aldehydes via a visible-light photocatalysis-hydrolysis sequence
    Hsu, Yin-Yin
    Luo, Sheng-Qi
    Hong, Bor-Cherng
    Chien, Su-Ying
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (16) : 3292 - 3302