دانلود کتاب Grignard Reagents and Transition Metal Catalysts: Formation of C-C Bonds by Cross-Coupling

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Grignard Reagents and Transition Metal Catalysts: Formation of C-C Bonds by Cross-Coopling
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Contents
Contributing Authors
Introduction
1. Grignard Reagents and Palladium
1.1 Introductuin
1.2 The Discovery and Development of Catalytic Cross-Coupling Reactions of Grignard Reagents
1.3 The Mechanism of the Cross-Coupling of Grignard Reagents Catalyzed by Palladium Complexes
1.4 Applications of Palladium-Catalyzed Grignard Cross-Coupling Reactions
1.4.1 Coupling of Arylmagnesium Compounds
1.4.1.1 With Aryl Electrophiles
1.4.1.2 With Vinyl Electrophiles
1.4.1.3 With Alkyl Electrophiles
1.4.1.4 With Alkynyl Electrophiles
1.4.2 Coupling of Vinylmagnesium Compounds
1.4.2.1 With Aryl Electrophiles
1.4.2.2 With Vinyl Electrophiles
1.4.2.3 With Alkyl Electrophiles
1.4.3 Coupling of Alkylmagnesium Compounds
1.4.3.1 With Aryl Electrophiles
1.4.3.2 With Vinyl Electrophiles
1.4.3.3 With Alkyl Electrophiles
1.4.3.4 With Alkynyl Electrophiles
1.4.4 Coupling of Alkynylmagnesium Compounds
1.4.4.1 With Vinyl Electrophiles
1.4.4.2 With Alkyl Electrophiles
1.5 Industrial Deployment of Palladium-Catalyzed Grignard Cross-Couplings
1.6 Applications in Target Synthesis
1.7 Summary, Conclusions and Outlook
References
2. Grignard Reagents and Nickel
2.1 Introduction
2.2 Coupling reactions of aryl Grignard reagents
2.2.1 With aryl derivatives
2.2.1.1 With aryl bromides and chlorides
Use of phosphine ligands
Use of bidentate P,N Ligands
Use of tridentate pincer ligands
Use of NHC carbenes as ligands
Heterogeneous catalysis
2.2.1.2 With aryl fluorides
2.2.1.3 With aryl thioethers
2.2.1.4 With aryl sulfones, sulfonates, sulfonamides
2.2.1.5 With aryl ethers
2.2.1.5.1 Aryl alkylethers and aryl silylethers
2.2.1.5.2 Aryl and alkenyl carbamates and phosphates
2.2.1.5.3 Diaryl sulfates and aryl sulfamates
2.2.1.5.4 Magnesium aryloates
2.2.2 With vinyl derivatives
2.2.2.1 Vinyl halides
2.2.2.2 With vinyl thioethers
2.2.2.3 With cyclic enol ethers
2.2.3 With alkynyl halides
2.2.4 Miscellaneous
2.2.4.1 With propargyl bromide
2.2.4.2 With α-bromoketones
2.2.4.3 Three component reaction
2.3 Coupling reactions of alkenyl Grignard reagents
2.3.1 With aryl derivatives
2.3.1.1 With aryl halides
2.3.1.2 With aryl sulfides
2.3.1.3 With aryl carbamates
2.3.2 With vinyl derivatives
2.3.2.1 With vinyl sulfones
2.3.2.2 With vinyl carbamates
2.3.3 With alkyl derivatives
2.3.4 Miscellaneous
2.3.4.1 Three component reactions
2.3.4.2 Ring-opening of cyclic ethers
2.4 Coupling reactions of Alkynyl Grignard Reagents
2.4.1 With alkyl halides
2.4.2 With alkynyl sulfones
2.4.3 With ethers
2.4.3.1 Aryl ethers
2.4.3.2 Enol derivatives
Enol ethers
Vinyl carbamates
2.5 Coupling reactions of Alkyl Grignard Reagents
2.5.1 With aryl derivatives
2.5.1.1 Aryl halides
2.5.1.2 Aryl sulfides
2.5.1.3 Aryl methyl ethers
2.5.1.4 Aryl phosphonates
2.5.2 With alkenyl derivatives
2.5.2.1 Alkenyl halides
2.5.2.2 Enol carbamates and phosphates
2.5.3 With alkyl derivatives
2.5.3.1 Alkyl halides
2.5.3.2 Sulfones
2.5.3.3 Alkyl ethers
2.5.3.4 Benzyl alcohols
2.6 Conclusion
References
Julien Legros, Bruno Figadère
3. Grignard Reagents and Iron
3.1 Introduction
3.2 Coupling reactions of alkyl Grignard reagents
3.2.1 With aryl derivatives
Aryl halides
Aryl pseudohalides
3.2.2 With alkyl derivatives
Alkyl halides
Alkyl ethers
3.2.3 With vinyl derivatives
Vinyl halides
Vinyl pseudohalides
3.2.4 With allyl and propargyl derivatives
Allyl phosphonates
Allyl ethers
Propargyl halides
Propargyl ethers
3.2.5 With carbonyl derivatives
Acyl chlorides
Thioesters
3.3 Coupling reactions of aryl Grignard reagents
3.3.1 With aryl derivatives
Aryl halides
Aryl sulfamates and tosylates
3.3.2 With alkyl derivatives
Alkyl halides
Sulfides
Sulfones and sulfonyl chlorides
3.3.3 With vinyl derivatives
Vinyl halides
Vinyl sulfides
3.3.4 With allyl and propargyl derivatives
Allyl and propargyl halides
Allyl sulfonyl chlorides
Allyl ethers
3.3.5 With benzyl halides
3.3.6 With alkynyl halides
3.3.7 With carbonyl derivatives
Acyl chlorides
Thioesters
Aroyl cyanides
3.4 Coupling reactions of alkenyl Grignard reagents
3.4.1 With alkyl halides
3.5 Coupling reactions of alkynyl Grignard reagents
3.5.1 With vinyl halides
3.5.2 With alkyl halides
3.6 Miscellaneous
3.6.1 Three-component reactions
3.6.2 CH activation
3.7 Mechanistic considerations
3.7.1 Double-electron transfer mechanism
3.7.2 Single-electron transfer mechanism
3.8 Conclusion
References
4. Grignard Reagents and Cobalt
4.1 Introduction
4.2 Coupling reactions of alkylmagnesium reagents
4.2.1 With aryl halides
4.2.2 With alkyl halides
4.2.3 With alkenyl species
4.2.3.1 Alkenyl halides
4.2.3.2 Alkenyl tellurides
4.2.4 With allylic ethers
4.2.5 With alkynyl halides
4.3 Coupling reactions of arylmagnesium reagents
4.3.1 With aryl halides
4.3.2 With alkyl halides
4.3.3 With alkenyl halides
4.3.4 With allylic ethers
4.4 Coupling reactions of allylmagnesium reagents
4.4.1 With aryl halides
4.4.2 With alkyl halides
4.4.3 With allylic ethers
4.5 Coupling reactions of alkynylmagnesium reagents
4.5.1 With alkyl halides
4.5.2 With alkenyl triflates
4.5.3 With alkynyl halides
4.6 Coupling reactions of alkenylmagnesium reagents
4.6.1 With alkyl halides
4.6.2 With alkenyl species
4.6.2.1 Alkenyl halides
4.6.2.2 Alkenyl triflates
4.7 Tandem cyclization/cross-coupling
4.7.1 With arylmagnesium halides
4.7.2 With alkylmagnesium halides
4.7.3 With alkenylmagnesium halides
4.7.4 With allylmagnesium halides
4.7.5 With alkynylmagnesium halides
4.8 Three-component reactions
4.9 Conclusion
References
5. Grignard reagents and Manganese
5.1 Introduction
5.2 Preparation and reactivity of organomanganese reagents [3h,i]
5.3 Reactions of alkyl Grignard reagents
5.3.1 With acyl chlorides
5.3.2 With enones
5.3.3 With alkyl halides
5.3.4 With aryl halides
5.3.5 With alkenyl halides
5.3.6 With alkynes
5.3.7 With 1,3-dienes
5.3.8 With allenes
5.4 Reactions of aryl and heteroaryl Grignard reagents
5.4.1 With acyl halides
5.4.2 With alkyl halides
5.4.3 With aryl halides
5.4.4 With alkenyl halides and pseudo-halides
5.4.5 Oxidative homocoupling
5.4.6 Oxidative heterocoupling with another Grignard reagent
5.4.7 Manganese-catalyzed carbometallation with aryl Grignard reagents
5.5 Coupling reactions of alkenyl Grignard reagents
5.5.1 With acyl halides
5.5.2 Oxidative homocoupling
5.5.3 Oxidative heterocoupling with another Grignard reagent
5.6 Cross-coupling of alkynyl Grignard reagents
5.6.1 Oxidative homocoupling
5.6.2 Oxidative heterocoupling with another Grignard reagent
5.7 Conclusion
References
6. Grignard reagents and Copper
6.1 Introduction
6.2 Coupling reactions from alkyl Grignard reagents (R\'MgX)
6.2.1 Coupling of alkyl Grignard reagents with alkyl halides or pseudo-halides derivatives (RX)
6.2.2 Coupling of alkyl Grignard reagents with vinyl halides or pseudo-halides derivatives (RX)
6.2.3 Coupling of alkyl Grignard reagents with heteroaryl halides derivatives (RX)
6.2.4 Coupling of alkyl Grignard reagents with alkynyl halides or pseudo-halides derivatives (RX)
6.2.5 Coupling of alkyl Grignard reagents with allylic substrates
6.3 Coupling reactions of aryl Grignard reagents [1, 2, 45]
6.3.1 Coupling of aryl Grignard reagents with alkyl derivatives
6.3.1.1 Coupling with alkyl halides or pseudo-halides (triflates, mesylates,…)
6.3.1.2 Coupling with alkyl phosphates
6.3.1.3 Coupling with alkyl sulfonalides and sulfonimides
6.3.2 Coupling of aryl Grignard reagents with vinyl derivatives
6.3.3 Coupling of aryl Grignard reagents with alkynyl derivatives
6.4 Coupling reactions of other Grignard reagents
6.4.1 Coupling reactions of vinyl Grignard reagents
6.4.2 Coupling reactions of allyl Grignard reagents
6.5 Conclusion
References
7. Grignard Reagents and Silver
7.1 Introduction
7.2 Coupling reactions of aryl Grignard reagents
7.2.1 With aryl Grignard reagents
7.2.1.1 Homocoupling
7.2.1.2 Heterocoupling
7.2.2 With alkyl halides
7.3 Coupling of vinyl Grignard reagents with alkyl halides
7.4 Coupling of alkyl Grignard reagents
7.4.1 With alkyl Grignard reagents
7.4.1.1 Intermolecular homocoupling
7.4.1.2 Intramolecular homocoupling
7.4.2 With alkyl halides
7.4.3 With vinyl halide
7.5 Mechanism
7.6 Conclusion
References
Index