v Catalytic Aminohalogenation of Alkenes and Alkynes

被引：355

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 [J].

Alix, Aurelien ;

Lalli, Claudia ;

Retailleau, Pascal ;

Masson, Geraldine .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (25) :10389-10392

[2] Organocatalytic Enantioselective Olefin Aminofluorination [J].

Appayee, Chandrakumar ;

Brenner-Moyer, Stacey E. .

ORGANIC LETTERS, 2010, 12 (15) :3356-3359

[3] Catalytic Enantioselective Alkene Aminohalogenation/Cyclization Involving Atom Transfer [J].

Bovino, Michael T. ;

Chemler, Sherry R. .

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 [J].

Cai, Yunfei ;

Liu, Xiaohua ;

Li, Jun ;

Chen, Weiliang ;

Wang, Wentao ;

Lin, Lili ;

Feng, Xiaoming .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (52) :14916-14921

[6] Catalytic Asymmetric Chloroamination Reaction of α,β-Unsaturated γ-Keto Esters and Chalcones [J].

Cai, Yunfei ;

Liu, Xiaohua ;

Jiang, Jun ;

Chen, Weiliang ;

Lin, Lili ;

Feng, Xiaoming .

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 [J].

Cai, Yunfei ;

Liu, Xiaohua ;

Hui, Yonghai ;

Jiang, Jun ;

Wang, Wentao ;

Chen, Weiliang ;

Lin, Lili ;

Feng, Xiaoming .

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 [J].

Chen, Feng ;

Tan, Chong Kiat ;

Yeung, Ying-Yeung .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (04) :1232-1235

[10] A highly enantioselective approach towards 2-substituted 3-bromopyrrolidines [J].

Chen, Jie ;

Zhou, Ling ;

Yeung, Ying-Yeung .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (19) :3808-3811

← 1 2 3 4 5 6 7 →