Recyclable Hypervalent Iodine Reagents in Modern Organic Synthesis

被引:20
作者
Rimi [1 ]
Soni, Sakshi [1 ]
Uttam, Bhawna [1 ]
China, Hideyasu [2 ]
Dohi, Toshifumi [3 ]
Zhdankin, Viktor V. [4 ]
Kumar, Ravi [1 ]
机构
[1] JC Bose Univ Sci & Technol, Dept Chem, YMCA,NH-2,Sect-6,Mathura Rd, Faridabad 121006, Haryana, India
[2] Nagahama Inst Bio Sci & Technol, Dept Med Biosci, Tamuracho Nagahama shi, Shiga 5260829, Japan
[3] Ritsumeikan Univ, Coll Pharmaceut Sci, 1-1-1 Nojihigashi, Shiga 5258577, Japan
[4] Univ Minnesota Duluth, Dept Chem & Biochem, Univ Dr 126 HCAMS, Duluth, MN 55812 USA
来源
SYNTHESIS-STUTTGART | 2022年 / 54卷 / 12期
基金
日本科学技术振兴机构; 日本学术振兴会; 美国国家科学基金会;
关键词
hypervalent iodine; recyclable reagents; polymer-supported; non-polymeric; ionic-liquid-supported; MOF hybrid; SUPPORTED IBX-AMIDE; HIGHLY SELECTIVE OXIDATION; FLUOROUS ALKYL IODIDES; M-IODOSYLBENZOIC ACID; IONIC-LIQUID; FACILE PREPARATION; BIS(TRIFLUOROACETATE) ADDUCTS; IODO-FUNCTIONALIZATION; ALPHA-TOSYLOXYLATION; EFFICIENT OXIDATION;
D O I
10.1055/s-0041-1737909
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Hypervalent iodine (HVI) reagents have gained much attention as versatile oxidants because of their low toxicity, mild reactivity, easy handling, and availability. Despite their unique reactivity and other advantageous properties, stoichiometric HVI reagents are associated with the disadvantage of generating non-recyclable iodoarenes as waste/co-products. To overcome these drawbacks, the syntheses and utilization of various recyclable hypervalent iodine reagents have been established in recent years. This review summarizes the development of various recyclable non-polymeric, polymer-supported, ionic-liquid-supported, and metal organic framework (MOF)-hybridized HVI reagents. 1 Introduction 2 Polymer-Supported Hypervalent Iodine Reagents 2.1 Polymer-Supported Hypervalent Iodine(III) Reagents 2.2 Polymer-Supported Hypervalent Iodine(V) Reagents 3 Non-Polymeric Recyclable Hypervalent Iodine Reagents 3.1 Non-Polymeric Recyclable Hypervalent Iodine(III) Reagents 3.2 Recyclable Non-Polymeric Hypervalent Iodine(V) Reagents 3.3 Fluorous Hypervalent Iodine Reagents 4 Ionic-Liquid/Ion-Supported Hypervalent Iodine Reagents 5 Metal Organic Framework (MOF)-Hybridized Hypervalent Iodine Reagents 6 Conclusion. © 2022 Georg Thieme Verlag. All rights reserved.
引用
收藏
页码:2731 / 2748
页数:18
相关论文
共 145 条
[1]   Synthetic use of poly[4-hydroxy(tosyloxy)iodo]styrenes [J].
Abe, S ;
Sakuratani, K ;
Togo, H .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (18) :6174-6177
[2]   Umpolung of halide reactivity: efficient (diacetoxyiodo)benzene-mediated electrophilic α-halogenation of 1,3-dicarbonyl compounds [J].
Akula, Ramulu ;
Galligan, Marc ;
Ibrahim, Hasim .
CHEMICAL COMMUNICATIONS, 2009, (45) :6991-6993
[3]   Oxidation of secondary alcohols using solid-supported hypervalent iodine catalysts [J].
Ballaschk, Frederic ;
Kirsch, Stefan F. .
GREEN CHEMISTRY, 2019, 21 (21) :5896-5903
[4]   A novel use of the recyclable polymer-supported IBX: an efficient chemoselective and regioselective oxidation of phenolic compounds. The case of hydroxytyrosol derivatives [J].
Bernini, Roberta ;
Mincione, Enrico ;
Crisante, Fernanda ;
Barontini, Maurizio ;
Fabrizi, Giancarlo .
TETRAHEDRON LETTERS, 2009, 50 (12) :1307-1310
[5]  
Brenelli, 2005, TETRAHEDRON LETT, V7, P833
[6]   Electrosynthesis Using a Recyclable Mediator-Electrolyte System Based on lonically Tagged Phenyl Iodide and 1,1,1,3,3,3-Hexafluoroisopropanol [J].
Broese, Timo ;
Francke, Robert .
ORGANIC LETTERS, 2016, 18 (22) :5896-5899
[7]   Functional organic-inorganic colloids modified by iodoxybenzoic acid [J].
Bromberg, Lev ;
Zhang, Hidan ;
Hatton, T. Alan .
CHEMISTRY OF MATERIALS, 2008, 20 (05) :2001-2008
[8]   Hypervalent organoiodine(v) metal-organic frameworks: syntheses, thermal studies and stoichiometric oxidants [J].
Bryant, Macguire R. ;
Richardson, Christopher .
DALTON TRANSACTIONS, 2020, 49 (16) :5167-5174
[9]   Iodosylbenzene Coordination Chemistry Relevant to Metal-Organic Framework Catalysis [J].
Cardenal, Ashley D. ;
Maity, Asim ;
Gao, Wen-Yang ;
Ashirov, Rahym ;
Hyun, Sung-Min ;
Powers, David C. .
INORGANIC CHEMISTRY, 2019, 58 (16) :10543-10553
[10]   Singlet oxygen generation from poly[4-diacetoxyiodo]styrene and hydrogen peroxide [J].
Catir, Mustafa .
TURKISH JOURNAL OF CHEMISTRY, 2017, 41 (04) :467-475