v Catalytic Aminohalogenation of Alkenes and Alkynes

被引：349
作者：
Chemler, Sherry R. [1 ]
Bovino, Michael T. [1 ]
机构：
[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
来源：
ACS CATALYSIS | 2013年 / 3卷 / 06期
基金：
美国国家卫生研究院;
关键词：
aminohalogenation; catalysis; enantioselelective; alkenes; alkynes; allenes; haloamines; haloamidation; COPPER(I)-CATALYZED INTRAMOLECULAR ADDITION; UNSATURATED N-CHLOROAMINES; CHIRAL PHOSPHORIC-ACID; STEREOSELECTIVE AMINOHALOGENATION; EFFICIENT SYNTHESIS; DOUBLE-BONDS; NITROGEN/CHLORINE SOURCE; BETA-NITROSTYRENES; BROMINE SOURCES; AMINOFLUORINATION;
D O I：
10.1021/cs400138b
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
Catalytic aminohalogenation methods enable the regio- and stereoselective vicinal difunctionalization of alkynes, allenes, and alkenes with amine and halogen moieties. A range of protocols and reaction mechanisms including organometallic, Lewis base, Lewis acid, and Bronsted acid catalysis have been disclosed, enabling the regio- and stereoselective synthesis of halogen-functionalized acyclic amines and nitrogen heterocycles. Recent advances including aminofluorination and catalytic enantioselective aminohalogenation reactions are summarized in this review.
引用
收藏
页码：1076 / 1091
页数：16
相关论文
共 66 条
  • [1] Highly Enantioselective Electrophilic α-Bromination of Enecarbamates: Chiral Phosphoric Acid and Calcium Phosphate Salt Catalysts
    Alix, Aurelien
    Lalli, Claudia
    Retailleau, Pascal
    Masson, Geraldine
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (25) : 10389 - 10392
  • [2] Organocatalytic Enantioselective Olefin Aminofluorination
    Appayee, Chandrakumar
    Brenner-Moyer, Stacey E.
    [J]. ORGANIC LETTERS, 2010, 12 (15) : 3356 - 3359
  • [3] Catalytic Enantioselective Alkene Aminohalogenation/Cyclization Involving Atom Transfer
    Bovino, Michael T.
    Chemler, Sherry R.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (16) : 3923 - 3927
  • [4] Brindle CS, 2013, CHEM SCI, V4, P2100, DOI [10.1039/C3SC50410G, 10.1039/c3sc50410g]
  • [5] Asymmetric Iodoamination of Chalcones and 4-Aryl-4-oxobutenoates Catalyzed by a Complex Based on Scandium(III) and a N,N′-Dioxide Ligand
    Cai, Yunfei
    Liu, Xiaohua
    Li, Jun
    Chen, Weiliang
    Wang, Wentao
    Lin, Lili
    Feng, Xiaoming
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (52) : 14916 - 14921
  • [6] Catalytic Asymmetric Chloroamination Reaction of α,β-Unsaturated γ-Keto Esters and Chalcones
    Cai, Yunfei
    Liu, Xiaohua
    Jiang, Jun
    Chen, Weiliang
    Lin, Lili
    Feng, Xiaoming
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (15) : 5636 - 5639
  • [7] Catalytic Asymmetric Bromoamination of Chalcones: Highly Efficient Synthesis of Chiral α-Bromo-β-Amino Ketone Derivatives
    Cai, Yunfei
    Liu, Xiaohua
    Hui, Yonghai
    Jiang, Jun
    Wang, Wentao
    Chen, Weiliang
    Lin, Lili
    Feng, Xiaoming
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (35) : 6160 - 6164
  • [8] Chen DJ, 2004, EUR J ORG CHEM, V2004, P3097
  • [9] C2-Symmetric Cyclic Selenium-Catalyzed Enantioselective Bromoaminocyclization
    Chen, Feng
    Tan, Chong Kiat
    Yeung, Ying-Yeung
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (04) : 1232 - 1235
  • [10] A highly enantioselective approach towards 2-substituted 3-bromopyrrolidines
    Chen, Jie
    Zhou, Ling
    Yeung, Ying-Yeung
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (19) : 3808 - 3811
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