An efficient chemo and regioselective oxidative nuclear bromination of activated aromatic compounds using lithium bromide and ceric ammonium nitrate

被引：91

作者：

Roy, SC ^{[1
]}

Guin, C

Rana, KK

Maiti, G

机构：

[1] Indian Assoc Cultivat Sci, Dept Organ Chem, Kolkata 700032, W Bengal, India

[2] Jadavpur Univ, Dept Chem, Kolkata 700032, W Bengal, India

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 39期

关键词：

chemo and regioselective; oxidative nuclear bromination; lithium bromide; ceric ammonium nitrate;

D O I：

10.1016/S0040-4039(01)01412-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild, efficient and highly chemo- and regioselective method for the bromination of electron rich aromatic molecules has been developed by electrophilic substitution of Br+, which was generated in situ from LiBr using ceric ammonium nitrate as the oxidant. Free aromatic amines remained unaffected under the reaction conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：6941 / 6942

页数：2

共 33 条

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[22] Silica-gel-supported ceric ammonium nitrate (CAN): A simple and efficient solid-supported reagent for oxidation of oxygenated aromatic compounds to quinones
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[23] A convenient and regioselective oxidative bromination of electron-rich aromatic rings using potassium bromide and benzyltriphenylphosphonium peroxymonosulfate under nearly neutral reaction conditions
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TETRAHEDRON LETTERS, 2007, 48 (07) : 1255 - 1259
[24] Silica gel supported catalytic ceric ammonium nitrate: A simple and efficient reagent for oxidation of oxygenated aromatic compounds to quinones in non-aqueous media.
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ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 223 : B175 - B175
[25] Thiocyanation of aromatic and heteroaromatic compounds using polymer-supported thiocyanate ion as the versatile reagent and ceric ammonium nitrate as the versatile single-electron oxidant
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[26] Electrophilic substitution reactions of indoles with carbonyl compounds using ceric ammonium nitrate: A novel and efficient method for the synthesis of di- and tri-indolylmethanes
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JOURNAL OF CHEMICAL RESEARCH, 2003, (02) : 72 - 74
[27] Ceric ammonium nitrate (CAN)-mediated oxidative cycloaddition of 1,3-dicarbonyls to conjugated compounds. Efficient synthesis of dihydrofurans, dihydrofurocoumarins, dihydrofuroquinolinones, dihydrofurophenalenones, and furonaphthoquinone natural products
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TETRAHEDRON, 2000, 56 (45) : 8845 - 8853
[28] THE EFFECT OF BROMIDE IONS ON THE REACTION OF ALKYLAROMATIC COMPOUNDS WITH CERIUM(IV) AMMONIUM-NITRATE IN ACETIC-ACID - AN EFFICIENT METHOD FOR THE SIDE-CHAIN BROMINATION OF TOLUENES WITH ELECTRON-WITHDRAWING SUBSTITUENTS
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[29] Direct and regioselective iodination and bromination of benzene, naphthalene and other activated aromatic compounds using iodine and bromine or their sodium salts in the presence of the Fe(NO3)3•1•5N2O4/charcoal system
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[30] A Simple and Efficient Synthesis of 3,4,5-Trisubstituted/N-Fused 1,2,4-Triazoles via Ceric Ammonium Nitrate Catalyzed Oxidative Cyclization of Amidrazones with Aldehydes Using Polyethylene Glycol as a Recyclable Reaction Medium
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