TiCl3/PhN2+-mediated radical addition of ethers to aldimines generated in situ under aqueous conditions

被引：25
作者：
Clerici, A
Cannella, R
Panzeri, W
Pastori, N
Regolini, E
Porta, O
机构：
[1] Politecn Milan, Dipartimento Chim Mat & Ingn Chim Giulio Natta, Sez Chim, I-20131 Milan, Italy
[2] Politecn Milan, CNR, Ist Chim Riconoscimento Mol, Sez A Quilico, I-20131 Milan, Italy
来源：
TETRAHEDRON LETTERS | 2005年 / 46卷 / 48期
关键词：
titanium trichloride; one-electron reduction; radical addition; aldimines; three-component reaction;
D O I：
10.1016/j.tetlet.2005.09.158
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Ti(III)-mediated one-electron reduction of phenyldiazonium cation, followed by phenyl radical alpha-H atom abstraction from ethers, leads to one-pot radical addition of ethers to the C-atom of imines generated in situ from the corresponding aldehydes and imines under aqueous conditions. The reaction is not limited to aromatic aldehydes and may be applied to imines generated in situ from formaldehyde and enolizable aldehydes. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：8351 / 8354
页数：4
相关论文
共 25 条
  • [1] [Anonymous], [No title captured]
  • [2] ELECTRON SPIN RESONANCE STUDIES .21. REACTIONS OF PHENYL AND SUBSTITUTED PHENYL RADICALS IN AQUEOUS SOLUTION
    BECKWITH, AL
    NORMAN, ROC
    [J]. JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1969, (04): : 403 - &
  • [3] Et3B- and Et2Zn-mediated radical additions to glyoxylate imines, compared stereoinductions
    Bertrand, MP
    Coantic, S
    Feray, L
    Nouguier, R
    Perfetti, P
    [J]. TETRAHEDRON, 2000, 56 (24) : 3951 - 3961
  • [4] One-pot four-component reaction:: Aqueous TiCl3/PhN2+-mediated alkyl radical addition to imines generated in situ
    Cannella, R
    Clerici, A
    Pastori, N
    Regolini, E
    Porta, O
    [J]. ORGANIC LETTERS, 2005, 7 (04) : 645 - 648
  • [5] ARYLATIVE AMINATION OF ALDEHYDES PROMOTED BY AQUEOUS TITANIUM TRICHLORIDE
    CLERICI, A
    PORTA, O
    [J]. TETRAHEDRON LETTERS, 1990, 31 (14) : 2069 - 2072
  • [6] TITANIUM(IV) CHLORIDE PROMOTED CONDENSATION OF ORTHO-AMINONITRILES WITH DELTA-VALEROLACTONE
    DESAI, MC
    THADEIO, PF
    [J]. TETRAHEDRON LETTERS, 1989, 30 (39) : 5223 - 5226
  • [7] Chiral N-acylhydrazones:: Versatile imino acceptors for asymmetric amine synthesis
    Friestad, GK
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (15) : 3157 - 3172
  • [8] Enantioselective radical addition to N-acyl hydrazones mediated by chiral Lewis acids
    Friestad, GK
    Shen, YH
    Ruggles, EL
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (41) : 5061 - 5063
  • [9] Addition of carbon-centered radicals to imines and related compounds
    Friestad, GK
    [J]. TETRAHEDRON, 2001, 57 (26) : 5461 - 5496
  • [10] Intermolecular addition of alkyl radicals to imines in the absence and in the presence of a Lewis acid
    Halland, N
    Jorgensen, KA
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (11): : 1290 - 1295
123