Iron-Catalysed Direct Aromatic Amination with N-Chloroamines

被引:7
|
作者
Douglas, Gayle E. [1 ,2 ]
Raw, Steven A. [3 ]
Marsden, Stephen P. [1 ,2 ]
机构
[1] Univ Leeds, Sch Chem, Leeds LS2 9JT, W Yorkshire, England
[2] Univ Leeds, Inst Proc Res & Dev, Leeds LS2 9JT, W Yorkshire, England
[3] AstraZeneca, Pharmaceut Dev, Macclesfield SK10 3RN, Cheshire, England
基金
英国工程与自然科学研究理事会;
关键词
Amination; Arylamines; Radicals; Homogeneous catalysis; Tetrahydroquinolines; C-H-AMINATION; VISIBLE-LIGHT; ATROPOISOMERIC P; ARENES; IMIDATION; AMIDATION; HETEROARENES; TETRAHYDROQUINOLINE; DEPROTECTION; PRECURSORS;
D O I
10.1002/ejoc.201900614
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An optimized procedure for the direct intra- and intermolecular amination of aromatic C-H bonds with aminium radicals generated from N-chloroamines under iron catalysis is reported. A range of substituted tetrahydroquinolines could be readily prepared, while extension to the synthesis of benzomorpholines was more limited in scope. A direct one-pot variant was developed, allowing direct formal oxidative N-H/C-H coupling.
引用
收藏
页码:5508 / 5514
页数:7
相关论文
共 50 条
  • [21] Stereoselective synthesis of N-alkylaziridines from N-chloroamines
    Bew, Sean P.
    Hughes, D. L.
    Palmer, Nicholas J.
    Savic, Vladimir
    Soapi, Katy M.
    Wilson, Martin A.
    CHEMICAL COMMUNICATIONS, 2006, (41) : 4338 - 4340
  • [22] BEHAVIOUR OF HYPOCHLORITE AND OF N-CHLOROAMINES AT THE DROPPING MERCURY ELECTRODE
    HELLER, K
    JENKINS, EN
    NATURE, 1946, 158 (4020) : 706 - 706
  • [23] REACTION OF TRIVALENT PHOSPHORUS-COMPOUNDS WITH N-CHLOROAMINES
    KOLODYAZHNYI, OI
    GOLOVATYI, OR
    ZHURNAL OBSHCHEI KHIMII, 1995, 65 (02): : 341 - 342
  • [24] NITROGEN INVERSION IN CYCLIC N-CHLOROAMINES AND N-METHYLAMINES
    LAMBERT, JB
    OLIVER, WL
    PACKARD, BS
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (04) : 933 - &
  • [25] An iron-catalysed hydrosilylation of ketones
    Nishiyama, Hisao
    Furuta, Akihiro
    CHEMICAL COMMUNICATIONS, 2007, (07) : 760 - 762
  • [26] RADICAL AMINATION OF ALKYLBENZENES AND METHYL CINNAMATE BY N-CHLOROAMINES FACTORS AFFECTING ORIENTATION ATTACK ON NUCLEUS AND ON SIDE CHAIN
    MINISCI, F
    GALLI, R
    GALLI, A
    BERNARDI, R
    CHIMICA & L INDUSTRIA, 1967, 49 (03): : 252 - &
  • [27] FORMAL DYOTROPIC REARRANGEMENTS OF N-CHLOROAMINES CATALYZED BY ALUMINA
    DAVIES, JW
    MALPASS, JR
    WALKER, MP
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (11) : 686 - 687
  • [28] Iron-catalysed Sonogashira reactions
    Pan, Changduo
    Luo, Fang
    Wang, Wenhui
    Ye, Zhishi
    Liu, Miaochang
    JOURNAL OF CHEMICAL RESEARCH, 2009, (08) : 478 - 481
  • [29] Iron-catalysed intramolecular C(sp3)-H amination of alkyl azides
    Wu, Kai
    Che, Chi-Ming
    CHEMICAL COMMUNICATIONS, 2024, 60 (95) : 13998 - 14011
  • [30] Iron-catalysed tritiation of pharmaceuticals
    Yu, Renyuan Pony
    Hesk, David
    Rivera, Nelo
    Pelczer, Istvan
    Chirik, Paul J.
    NATURE, 2016, 529 (7585) : 195 - 199