Hypervalent iodine(III) reagents in organic synthesis

被引：353

作者：

Zhdankin, Viktor V. ^{[1
]}

机构：

[1] Univ Minnesota, Dept Chem & Biochem, Duluth, MN 55812 USA

来源：

ARKIVOC | 2009年

基金：

美国国家科学基金会;

关键词：

Hypervalent iodine; oxidation; (difluoroiodo)benzene; (dichloroiodo)benzene; iodosylbenzene; (diacetoxyiodo)benzene; hydroxy(tosyloxy)]iodobenzene; catalysis; recyclable reagents; M-CHLOROPERBENZOIC ACID; ONE-POT SYNTHESIS; ANOMERIC ALKOXYL RADICALS; IN-SITU GENERATION; POLYVALENT ORGANOIODINE COMPOUNDS; HIGHLY SELECTIVE OXIDATION; DIRECT ALPHA-HYDROXYLATION; ASYMMETRIC TOTAL SYNTHESES; P-IODOTOLUENE DIFLUORIDE; FLUOROUS ALKYL IODIDES;

D O I：

10.3998/ark.5550190.0010.101

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This review summarizes the chemistry of hypervalent iodine (III) compounds with emphasis of their synthetic applications. The preparation and reactions of (difluoroiodo)arenes, (dichloroiodo)arenes, iodosylarenes, [bis (acyloxy)iodo] arenes, and aryliodine (III) organosulfonates are overviewed. Application of these reagents allows mild and highly selective oxidative transformations in a facile and environmentally friendly manner. Some of these useful transformations can be carried out using organoiodine (III) compounds as catalysts or recyclable reagents.

引用

页码：1 / 62

页数：62

共 360 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] A highly chemoselective oxidation of alcohols to carbonyl products with iodosobenzene diacetate mediated by chromium(III)(salen) complexes:: Synthetic and mechanistic aspects [J].

Adam, W ;

Hajra, S ;

Herderich, M ;

Saha-Möller, CR .

ORGANIC LETTERS, 2000, 2 (18) :2773-2776

[3] Hypervalent iodine in the synthesis of bridgehead heterocycles: A facile route to the synthesis of 6-arylimidazo[2,1-b]thiazoles using [hydroxy(tosyloxy)iodo]benzene [J].

Aggarwal, R ;

Sumran, G .

SYNTHETIC COMMUNICATIONS, 2006, 36 (07) :875-879

[4] Efficient conversion of ketones to α-tosyloxyketones with m-chloroperbenzoic acid and p-toluenesulfonic acid in the presence of catalytic amount of IL-Supported phl in [emim]OTs [J].

Akiike, Junnosuke ;

Yamamoto, Yukiharu ;

Togo, Hideo .

SYNLETT, 2007, (14) :2168-2172

[5] Palladium-catalyzed ring-forming aminoacetoxylation of alkenes [J].

Alexanian, EJ ;

Lee, C ;

Sorensen, EJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (21) :7690-7691

[6] Alkoxyl radical fragmentation of 3-azido-2,3-dideoxy-2-halo-hexopyranoses:: a new entry to chiral polyhydroxylated 2-azido-1-halo-1-alkenes [J].

Alonso-Cruz, Carmen R. ;

Kennedy, Alan R. ;

Rodriguez, Maria S. ;

Suarez, Ernesto .

TETRAHEDRON LETTERS, 2007, 48 (40) :7207-7210

[7] Fragmentation of carbohydrate anomeric alkoxyl radicals.: Synthesis of highly functionalized chiral vinyl sulfones [J].

Alonso-Cruz, CR ;

León, EI ;

Ortiz-López, FJ ;

Rodríguez, MS ;

Suárez, E .

TETRAHEDRON LETTERS, 2005, 46 (32) :5265-5268

[8] Fragmentation of carbohydrate anomeric alkoxyl radicals.: A new synthesis of chiral β-lodo azides, vinyl azides, and 2H-azirines [J].

Alonso-Cruz, CR ;

Kennedy, AR ;

Rodríguez, MS ;

Suárez, E .

ORGANIC LETTERS, 2003, 5 (20) :3729-3732

[9] Production of piperonal, vanillin, and p-anisaldehyde via solventless supported iodobenzene diacetate oxidation of isosafrol, isoeugenol, and anethol under microwave irradiation [J].

Alvarez, Heiddy Marquez ;

Barbosa, Dayse P. ;

Fricks, Alini Tinoco ;

Aranda, Donato A. G. ;

Valdes, Ricardo H. ;

Antunes, O. A. C. .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2006, 10 (05) :941-943

[10] Oxidative access to quinolinone derivatives with simultaneous rearrangement of functional groups [J].

Amano, Yoshiharu ;

Inoue, Keisuke ;

Nishiyama, Shigeru .

SYNLETT, 2008, (01) :134-136

← 1 2 3 4 5 6 7 8 9 10 →