Hypervalent Iodine-Catalyzed Oxidative Functionalizations Including Stereoselective Reactions

被引:304
作者
Singh, Fateh V. [1 ]
Wirth, Thomas [1 ]
机构
[1] Cardiff Univ, Sch Chem, Cardiff CF10 3AT, S Glam, Wales
关键词
catalytic oxidations; hypervalent iodine; oxidants; rearrangement; stereoselective reactions; M-CHLOROPERBENZOIC ACID; O-IODOXYBENZOIC ACID; P-TOLUENESULFONIC ACID; IN-SITU GENERATION; DESS-MARTIN PERIODINANE; ENANTIOSELECTIVE ALPHA-TOSYLOXYLATION; ELECTROLYTIC PARTIAL FLUORINATION; ANODIC GEM-DIFLUORINATION; METAL-FREE; ORGANIC-SYNTHESIS;
D O I
10.1002/asia.201301582
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Hypervalent iodine chemistry is now a well-established area of organic chemistry. Novel hypervalent iodine reagents have been introduced in many different transformations owing to their mild reaction conditions and environmentally friendly nature. Recently, these reagents have received particular attention because of their applications in catalysis. Numerous hypervalent iodine-catalyzed oxidative functionalizations such as oxidations of various alcohols and phenols, -functionalizations of carbonyl compounds, cyclizations, and rearrangements have been developed successfully. In these catalytic reactions stoichiometric oxidants such as mCPBA or oxone play a crucial role to generate the iodine(III) or iodine(V) species in situ. In this Focus Review, recent developments of hypervalent iodine-catalyzed reactions are described including some asymmetric variants. Catalytic reactions using recyclable hypervalent iodine catalysts are also covered.
引用
收藏
页码:950 / 971
页数:22
相关论文
共 197 条
[11]  
[Anonymous], 2010, ANGEW CHEM INT ED, DOI DOI 10.1002/ANGE.200907352
[12]  
Antonchick A. P., 2011, ANGEW CHEM, V123, P8764
[13]   Organocatalytic, Oxidative, Intramolecular C-H Bond Amination and Metal-free Cross-Amination of Unactivated Arenes at Ambient Temperature [J].
Antonchick, Andrey P. ;
Samanta, Rajarshi ;
Kulikov, Katharina ;
Lategahn, Jonas .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (37) :8605-8608
[14]   Identification of anti-inflammatory diterpenes from the marine gorgonian Pseudopterogorgia elisabethae [J].
Ata, A ;
Kerr, RG ;
Moya, CE ;
Jacobs, RS .
TETRAHEDRON, 2003, 59 (23) :4215-4222
[15]   Quinols as novel therapeutic agents. 2. 4-(1-arylsulfonylindol-2-yl)-4-hydroxycyclohexa-2,5-dien-1-ones and related agents as potent and selective antitumor agents [J].
Berry, JM ;
Bradshaw, TD ;
Fichtner, I ;
Ren, RB ;
Schwalbe, CH ;
Wells, G ;
Chew, EH ;
Stevens, MFG ;
Westwell, AD .
JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (02) :639-644
[16]   Organocatalysis-after the gold rush [J].
Bertelsen, Soren ;
Jorgensen, Karl Anker .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (08) :2178-2189
[17]   Terminal Olefins to Linear α,β-Unsaturated Ketones: Pd(II)/Hypervalent Iodine Co-catalyzed Wacker Oxidation-Dehydrogenation [J].
Bigi, Marinus A. ;
White, M. Christina .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (21) :7831-7834
[18]   Hypervalent iodine mediated intramolecular cyclization of thioformanilides: Expeditious approach to 2-substituted benzothiazoles [J].
Bose, D. Subhas ;
Idrees, Mohd. .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (21) :8261-8263
[19]   Dess-Martin Periodinane Mediated Intramolecular Cyclization of Phenolic Azomethines: A Solution-Phase Strategy toward Benzoxazoles and Benzothiazoles [J].
Bose, D. Subhas ;
Idrees, Mohd .
SYNTHESIS-STUTTGART, 2010, (03) :398-402
[20]   Ortho-substituted iodobenzenes as novel organocatalysts for bromination of alkenes [J].
Braddock, D. Christopher ;
Cansell, Gemma ;
Hermitage, Stephen A. .
CHEMICAL COMMUNICATIONS, 2006, (23) :2483-2485