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Addressing a dynamic aspect of organic chemistry, this book describes synthetic strategies and applications for multicomponent reactions - including key routes for synthesizing complex molecules.
* Illustrates the crucial role and the important utility of multicomponent reactions (MCRs) to organic syntheses
* Compiles novel and efficient synthetic multicomponent procedures to give readers a complete picture of this class of organic reactions
* Helps readers to design efficient and practical transformations using multicomponent reaction strategies
* Describes reaction background, applications to synthesize complex molecules and drugs, and reaction mechanisms
List of contents
List of Contributors xii
Preface xiii
List of Abbreviations xv
1 Introduction: Multicomponent Strategies 1
General Introduction 1
1.1 Basic Concepts 3
1.1.1 Clarifying Terminology: One?]Pot, Domino/Cascade, Tandem, and MCRs 3
1.1.2 Using Rational Design to Discover New MCRs 3
1.1.3 Discovering New MCRs with Automated Combinatorial Reaction Finding 5
1.1.4 Computational and Analytical Tools to Study MCRs 7
1.1.5 Diversity?]Oriented Synthesis and Biology?]Oriented Synthesis 7
1.1.6 Optimization of MCRs 7
1.2 Catalysis in MCRs and Various Synthetic Approaches 8
1.2.1 Organocatalysis in MCRs 8
1.2.2 Organometallic Catalysis in MCRs 8
1.2.3 Biocatalysis in MCRs 8
1.2.4 Combining Different Types of Catalysis 8
1.2.5 Other Methods 9
1.3 Green Chemistry 10
1.3.1 Atom Economy 10
1.3.2 Using Green Solvents 11
1.3.3 Solventless MCRs 11
1.3.4 Heterogeneous Catalysis in MCRs 11
1.4 Importance and Evolution 12
References 12
2 Organocatalytic Asymmetric Multicomponent Reactions 16
2.1 Introduction 16
2.2 Three?]Component Mannich Reaction 17
2.3 Cycloaddition Reaction 26
2.4 Organocatalytic Multicomponent Domino Asymmetric Reactions 29
2.4.1 Michael?]Type Multicomponent Process: Cyclic Carbon Frameworks 30
2.4.2 Miscellaneous Domino Reactions 49
2.5 Development of Drug Intermediates 58
2.6 Miscellaneous Reaction 65
2.7 Conclusions 66
References 66
3 Metal?]Catalyzed Multicomponent Reactions 72
3.1 Introduction 72
3.2 Palladium?]Catalyzed Mcrs 72
3.2.1 Palladium?]Catalyzed Carbonylation Reactions 72
3.2.2 Palladium?]Catalyzed Mcrs Involving Isocyanides 74
3.2.3 Carbopalladation of Unsaturated C"?C pi?]Components 76
3.2.4 Amines as Building Blocks 80
3.3 Nickel?]Catalyzed Mcrs 83
3.3.1 Nickel?]Catalyzed Cross?]Trimerization of Alkynes 83
3.3.2 Nickel?]Catalyzed pi?]Systems Couplings 86
3.3.3 Ni?]Catalyzed Reductive Conjugate Addition 88
3.4 Group 11 Metal?]Catalyzed Mcrs 91
3.4.1 Copper?]Catalyzed Azide-Alkyne Cycloaddition 91
3.4.2 A3?]Coupling 94
3.4.3 Miscellaneous 101
3.5 Rhodium?]Catalyzed Mcrs 101
3.5.1 Rhodium?]Catalyzed Mcrs via Onium Ylide Intermediates 101
3.5.2 Rhodium?]Catalyzed Three?]Component Cross?]Addition Reactions 108
3.6 Group 8 Metal?]Catalyzed Mcrs 111
3.6.1 Iron?]Catalyzed Mcrs 111
3.6.2 Ruthenium?]Catalyzed Mcrs 113
3.7 Conclusions 117
References 117
4 Multicomponent Reactions with Organoboron Compounds 127
4.1 Introduction 127
4.2 Catalytic Mcrs with Organoboron Compounds 127
4.2.1 Cobalt?]Catalyzed Mcrs Containing Organoboron Compounds 127
4.2.2 Palladium?]Catalyzed Mcrs Containing Organoboron Compounds 128
4.3 Multicomponent Assembly of Organoboron Compounds: Efficient Approach to Supramolecular Chemistry 128
4.4 Multicomponent Petasis?]Borono-Mannich Reaction 132
4.4.1 Organocatalytic Enantioselective Petasis?]Type Reaction 133
4.4.2 Metal?]Catalyzed Four?]Component PBM Reaction 134
4.4.3 Synthetic Applications of PBM 135
4.5 Allenylborates in Mcrs 140
4.6 Multicomponent Hetero?]Diels-Alder/Allylboration 141
4.6.1 Chiral Catalyzed One?]Pot [4 + 2] Cycloaddition/Allylboration 141
4.6.2 Polymer?]Suppo
About the author
Raquel P. Herrera, PhD, is Tenured Scientist of the Spanish National Research Council (CSIC) at the ISQCH-University of Zaragoza. Her research interests are focused on asymmetric organocatalysis and its applications.
Eugenia Marqués-López, PhD, is an assistant professor at the University of Zaragoza. She performs her research on new catalytic methods, mainly based on asymmetric organocatalysis at the Institute of Chemical Synthesis and Homogeneous Catalysis (ISQCH-CSIC).
Summary
Addressing a dynamic area of organic chemistry, this book describes synthetic strategies and applications for multicomponent reactions. It illustrates the crucial role and the important utility of multicomponent reactions (MCRs) to organic syntheses.
