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Synthesis 1990; 1990(6): 431-447
DOI: 10.1055/s-1990-26898
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Carbon-Carbon Bond Formation Via Hypervalent Iodine Oxidations

Robert M. Moriarty* , Radhe K. Vaid
  • *Department of Chemistry, University of Illinois at Chicago, Chicago, IL. 60680, USA
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Publication Date:
17 September 2002 (online)

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A variety of hypervalent iodine(III) reactions which are useful for the formation of the carbon-carbon bond are reviewed. 1. Introduction 2. Intramolecular Carbocyclization 3. Synthesis of 1,4-Diketones 4. Self-Coupling of β-Dicarbonyl Compounds 5. Synthesis of 3-Aroyl-5-aryl-2-hydroxyfurans 6. Allylation of Aromatic Compounds 7. Synthesis of Azaanthraquinonespirodienones 8. Oxidative Coupling of Reticuline to Salutaridine 9. Pummerer-Type Reaction of α-Methylthio Using [Bis(trifluoroacetoxy)iodo] benzene 10. Ylides 10.1. Reactions of Iodonium Ylides Derived from β-Dicarbonyl Compounds 10.2. Reactions of 4,6-Dinitro-2-(phenyliodonio)phenolate 10.3. Reactions of [Bis(phenylsulfonyl)]phenyliodoniomethanide 11. Iodonium Salts 11.1. Reactions of Alkenyliodonium Salts 11.2. Reactions of Alkynyliodonium Salts 11.3. Perfluoroalkylations 11.4. Reactions of Indolyliodonium salts 11.5. C-Arylation of Various Substrates Using Diaryliodonium Salts 11.6. Generation of Benzyne and Its Reactions 12. Conclusion