Functionalization of 2-bromo-N-benzyl indole via lithium-bromide exchange

被引：3
作者：
Feldman, Ken S. [1 ]
Gonzalez, Inanllely Y. [1 ]
Brown, Jocelyn E. [1 ]
机构：
[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA
来源：
TETRAHEDRON LETTERS | 2015年 / 56卷 / 23期
基金：
美国国家科学基金会;
关键词：
N-Benzyl indole; Lithium-bromide exchange; Nucleophilic addition; n-BuLi; ALKENES;
D O I：
10.1016/j.tetlet.2015.01.032
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The carbofunctionalization of 2-bromo-N-benzyl indole via lithium-bromide exchange is presented. The reaction scope is demonstrated by providing a variety of substrate examples that deliver carbofunctionalized products in good-to-excellent yields. The competition between nucleophilic addition and proton transfer is discussed. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3564 / 3566
页数：3
相关论文
共 17 条
  • [1] [Anonymous], 2009, BOSTON NEWS LETT
  • [2] METAL-HALOGEN INTERCHANGE BETWEEN TERT-BUTYLLITHIUM AND 1-IODO-5-HEXENES PROVIDES NO EVIDENCE FOR SINGLE-ELECTRON TRANSFER
    BAILEY, WF
    PATRICIA, JJ
    NURMI, TT
    WANG, W
    [J]. TETRAHEDRON LETTERS, 1986, 27 (17) : 1861 - 1864
  • [3] Crespo A., 2012, PCT Int. Appl., Patent No. 2012097744
  • [4] The synthesis of indolo- and pyrrolo[2,1-a]isoquinolines
    de Koning, CB
    Michael, JP
    Pathak, R
    van Otterlo, WAL
    [J]. TETRAHEDRON LETTERS, 2004, 45 (06) : 1117 - 1119
  • [5] Intramolecular [3+2] Cyclocondensations of Alkenes with Indolidenes and Indolidenium Cations
    Feldman, Ken S.
    Gonzalez, Inanllely Y.
    Glinkerman, Christopher M.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (43) : 15138 - 15141
  • [6] Hemalathaa K., 2013, Che Sci, V2, P287
  • [7] JULIA M, 1970, CR ACAD SCI C CHIM, V270, P838
  • [8] CARBON-DIOXIDE - A REAGENT FOR THE PROTECTION OF NUCLEOPHILIC CENTERS AND THE SIMULTANEOUS ACTIVATION OF ALTERNATIVE LOCATIONS TO ELECTROPHILIC ATTACK .1. A NEW SYNTHETIC METHOD FOR THE 2-SUBSTITUTION OF 1-UNSUBSTITUTED INDOLES
    KATRITZKY, AR
    AKUTAGAWA, K
    [J]. TETRAHEDRON LETTERS, 1985, 26 (48) : 5935 - 5938
  • [9] Synthesis of the dibenzopyrrocoline alkaloid skeleton:: indolo-[2,1-A]isoquinolines and related analogues
    Lotter, Angelique N. C.
    Pathak, Rakhi
    Sello, Thato S.
    Fernandes, Manuel A.
    van Otterlo, Willem A. L.
    de Koning, Charles B.
    [J]. TETRAHEDRON, 2007, 63 (10) : 2263 - 2274
  • [10] Benzannulation reactions of Fischer carbene complexes for the synthesis of indolocarbazoles
    Merlic, CA
    You, Y
    McInnes, DM
    Zechman, AL
    Miller, MM
    Deng, Q
    [J]. TETRAHEDRON, 2001, 57 (24) : 5199 - 5212
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