Iron-Catalyzed Reactions in Organic Synthesis.pdf

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Iron-Catalyzed Reactions in Organic Synthesis.pdf

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Iron-Catalyzed Reactions in Organic Synthesis

Iron-Catalyzed Reactions in Organic Synthesis Carsten Bolm,* Julien Legros, Jacques Le Paih, and Lorenzo Zani Institut fu?r Organische Chemie der Rheinisch-Westfa?lischen Technischen Hochschule Aachen, Professor-Pirlet-Strasse 1, D-52056 Aachen, Germany Received June 24, 2004 Contents 1. Introduction 6217 2. Addition Reactions 6218 2.1. Aldol Reactions and Related Processes 6218 2.2. Michael Additions and Other Conjugate Addition Reactions 6220 2.3. Allylations of Carbonyl Compounds and Acetals 6222 2.4. Carbometalations 6224 2.5. Nazarov Cyclizations 6224 2.6. Barbier-Type Reactions 6225 2.7. Additions of Halocarbons to Double Bonds (Kharasch Reaction) 6226 2.8. Addition by Means of C?H Activation 6228 2.9. Ring Opening Reactions 6228 2.10. Acetalizations and Related Protection Methodologies 6230 3. Substitution Reactions 6231 3.1. Electrophilic Substitutions 6231 3.2. Nucleophilic Substitutions 6231 3.2.1. SN Processes 6231 3.2.2. SRN Processes 6232 3.3. Cross-Coupling Reactions 6233 3.3.1. Alkenyl Derivatives as Substrates 6234 3.3.2. Aryl Derivatives as Substrates 6235 3.3.3. Alkyl Derivatives as Substrates 6236 3.3.4. Acyl Derivatives as Substrates 6236 3.4. Conversions of Ethers into Acetates 6237 4. Cycloadditions 6237 4.1. [2+1]-Cycloadditions 6237 4.2. [2+2]-Cycloadditions 6238 4.3. [2+2+1]-Cycloadditions 6238 4.4. [2+2+2]-Cycloadditions 6238 4.5. [4+1]-Cycloadditions 6239 4.6. [4+2]-Cycloadditions 6239 4.7. [4+4]-Cycloadditions 6240 4.8. Ene Carbocyclization 6240 4.9. 1,3-Dipolar Cycloadditions 6241 5. Hydrogenations and Reductions 6241 5.1. Hydrogenations 6241 5.2. Reduction of Nitroarenes to Aniline Derivatives 6241 5.3. Reduction of Aryl and Alkenyl Halides 6242 6. Isomerizations and Rearrangements 6242 6.1. Double Bond Isomerizations 6242 6.2. Ring Rearrangements 6243 7. Polymerizations 6243 7.1. Ethylene Polymerizations and Related Processes 6243 7.2. Olefin Polymerizations via ATRP Reactions 6244 7.3. Other Polymerizations 6245 8. Miscellaneous 6246