Multicomponent Reactions
Editat de Mariateresa Giustinianoen Limba Engleză Hardback – 16 sep 2026
Multicomponent reactions enable the combination of three or more starting materials in a single vessel to afford diverse and complex products while aligning with green chemistry principles. This two-volume work summarizes the most recent MCR applications and emerging trends, providing expert knowledge on current advancements across organic chemistry, medicinal chemistry, polymer and analytical chemistry.
The book explores sustainable chemical approaches, such as electrochemistry, photochemistry, mechanochemistry, and flow chemistry. It also covers biocatalytic MCRs, reactions in non-conventional solvents, isotope labeling, and late-stage functionalization.
Additional topics include:
* Artificial intelligence and automated synthesis (HTS) enhancing MCRs workflows in research laboratories
* Drug discovery applications demonstrating how MCRs rapidly generate diverse chemical libraries of heterocycles and bioactive compounds, including protein degraders
* Reactive intermediates and reaction mechanisms in multicomponent processes
* Innovative approaches for designing advanced materials with specific functional properties
* MCRs in chemical education
This comprehensive book will benefit organic chemists, medicinal chemists, materials scientists, and chemical engineers, providing them with practical knowledge of sustainable synthetic methods from expert contributors across various research fields.
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Specificații
Notă biografică
Mariateresa Giustiniano is an associate professor at the University of Naples Federico II in Italy. She has co-authored over 60 peer-reviewed publications and four book chapters, with research interests spanning multicomponent reactions, visible-light photocatalysis, and their application in medicinal chemistry for discovering new anticancer agents.
Cuprins
Contents Volume 1
Preface xi
1 Multicomponent Reactions for a Sustainable Organic Synthesis 1
Elena Cassera, Davide Ravelli, Mariateresa Giustiniano, and Maurizio Fagnoni
1.1 Introduction 1
1.2 Passerini Reaction 4
1.3 Ugi Reaction 9
1.4 Ugi-Joullié Reaction 15
1.5 Greenness of MCRs in Drug Preparation 21
1.6 Conclusion and Outlook 24
2 Light-triggered Multicomponent Reactions 33
Lorenzo Di Terlizzi and Stefano Protti
2.1 Introduction 33
2.2 Photoredox Catalyzed MCRs 34
2.3 MCRs via Direct (d-HAT) or Indirect (i-HAT) Hydrogen Atom Transfer 40
2.4 MCRs via Halogen Atom Transfer 42
2.5 MCRs via Energy Transfer 45
2.6 Photochemical MCRs 46
2.7 Conclusions 50
3 Multicomponent Electrochemical Strategies for Modern Organic Synthesis 55
Rajesh Kumar, Vinay Thatikonda, and Upendra K. Sharma
3.1 Introduction 55
3.2 Electrochemical Alkene Dicarbofunctionalization 56
3.3 Multicomponent Electrochemical Alkene Hetero-Difunctionalization 58
3.4 Four-component Electrochemical Alkene Difunctionalization 63
3.5 Multicomponent Electrochemical Synthesis of Five-membered N-Heterocycles 65
3.6 Gases as Renewable Feedstocks in Electrocatalysis 69
3.7 Conclusion 75
4 Mechanochemical Multicomponent Reactions 79
Francesco Basoccu, Dipak J. Fartade, and Andrea Porcheddu
4.1 Introduction 79
4.2 Classical Mechanochemical MCRs 80
4.3 Pseudo-MCRs 95
4.4 Miscellaneous 103
4.5 Limitations and Challenges 110
4.6 Future Perspective 110
4.7 Conclusion 111
5 The Use of Microwave-assisted Multicomponent Reactions for the Synthesis of Heterocycles Containing Isatin or Organophosphorus Moiety 119
Dániel Steinsits and Erika Bálint
5.1 Introduction 119
5.2 Microwave-assisted Multicomponent Reactions of Isatins 121
5.3 Synthesis of Heterocycles Containing Organophosphorus Moiety 130
5.4 Summary and Conclusions 135
6 Biocatalytic Multicomponent Reactions 141
Camilla Russo, Flora Antoniou, and Daniele Castagnolo
6.1 Introduction 141
6.2 "True" Biocatalytic Multicomponent Reactions 143
6.3 Combined Biocatalytic Multicomponent Approaches 161
6.4 Summary and Conclusions 172
7 Isocyanide-based Multicomponent Reactions in Aqueous Media 185]
Mohammad Taghi Nazeri, Tahereh Nasiriani, Nuhaa Shaheed, and Ahmad Shaabani
7.1 Introduction 185
7.2 Synthesizing Cyclic Compounds 187
7.3 Synthesizing Acyclic Compounds 216
7.4 Challenges and Future Perspective in Water-based Media 230
7.5 Conclusion 231
8 Non-Isocyanide-based Multicomponent Reactions in Aqueous Media 243
Mohammad Taghi Nazeri, Tahereh Nasiriani, Nuhaa Shaheed, and Ahmad Shaabani
8.1 Introduction 243
8.2 Synthesizing Cyclic Compounds 245
8.3 Synthesizing Acyclic Compounds 267
8.4 Future Directions: Integrating Emerging Technologies 285
8.5 Conclusion 287
9 The Use of Nonconventional Solvents in Multicomponent Reactions 301
Yavar Ahmadi and Ali Ramazani
9.1 Introduction 301
9.2 Properties and Structure of Deep Eutectic Solvents 305
9.3 Multicomponent Reactions 307
9.4 DES in Multicomponent Reactions 308
9.5 Perspectives and Conclusions 317
10 Nanoreactors Technology in Multicomponent Reactions 325
Seyedmohammad Hosseininezhad, Melika Seydi, and Ali Ramazani
10.1 Introduction 325
10.2 Overview of MCRs 326
10.3 Overview of Nanoreactors 333
10.4 Applications of Nanoreactors in Key MCRs 336
10.5 Conclusion 364
10.6 Future Perspectives and Emerging Trends 365
11 Multicomponent Reactions in Automated Synthetic Chemistry 375
Imma Capriello and Alexander Dömling
11.1 Why Automation? 375
11.2 Why Miniaturization? 379
11.3 Integrating Platforms 385
11.4 The Future of Automated and Miniaturized Organic Synthesis 398
Contents Volume 2
Preface xi
12 Scale-up and Automation of Multicomponent Reactions via Continuous Flow 405
Johannes Bingold, Andreas Brunschweiger, and Norbert Kockmann
12.1 Introduction, Motivation, and Overview 405
12.2 Flow Reactions and Reactor Systems 406
12.3 Exemplary Multicomponent Reactions Performed in Flow 413
12.4 Scale-up Conditions for MCR Flow Chemistry 421
12.5 Scale-up Examples in API Synthesis 425
12.6 Summary and Conclusions 426
13 Investigating Multicomponent Reactions Mechanisms 435
Brenno A. D. Neto, Giovanni W. Amarante, and Alexandre A. M. Lapis
13.1 Introduction 435
13.2 Terminology Definitions 437
13.3 The Reaction Pathway Control 438
13.4 Mass Spectrometry-The Key Analysis to Understand MCRs 439
13.5 Examples of Pioneering Works 440
13.6 Examples of Mechanistic Studies of Well-established MCRs 444
13.7 Selected Examples 448
13.8 Outlook 450
14 Reactive Intermediates in Isocyanide-based Multicomponent Reactions 457
Ana G. Neo and Carlos F. Marcos
14.1 Introduction 457
14.2 Primary Adducts 458
14.3 Other Intermediates 473
14.4 Summary and Conclusions 480
15 Heterocycle-based Multicomponent Reactions 489
Pau Nadal-Rodríguez, Ouldouz Ghashghaei, and Rodolfo Lavilla
15.1 Introduction and Scope 489
15.2 Conceptual Approaches 490
15.3 Polar MCRs 492
15.4 Radical MCRs 494
15.5 Metal-catalyzed MCRs 497
15.6 Concerted MCRs 500
15.7 Applications 501
15.8 Summary and Outlook 503
16 Multicomponent Synthesis of Functional Chromophores 513
Larissa Brandner and Thomas J. J. Müller
16.1 Functional Chromophores 513
16.2 Scaffold and Chromophore Approach 514
16.3 MCR to Functional Chromophores Based on Carbonyl Compounds 515
16.4 MCR to Functional Chromophores Based on Isonitriles 524
16.5 MCR to Functional Chromophores Based on Cycloadditions 529
16.6 MCR to Functional Chromophores Based on Radical Reactions 531
16.7 MCR to Functional Chromophores Based on Metal-mediated and Metal-catalyzed Reactions 532
16.8 Conclusion and Outlook 536
17 Atropisomers and Molecular Balances via Multicomponent Reactions 543
Michael Fragkiadakis, Michael Kapsalis, and Constantinos Neochoritis
17.1 Introduction 543
17.2 Atropisomerism via Axis Generation 546
17.3 Atropisomerism via Rigid Molecular Frameworks 554
17.4 Atropisomerism via Specific Non-covalent Interactions 556viii Contents Volume 2
17.5 Summary and Conclusions 561
18 Multicomponent Synthesis of Organoselenium Compounds 565
Paola S. Hellwig, Thiago A. Ribeiro, Mateus W. Rambo, Kethelyn M. Rosa, Nicole M. N. Washio, Ricardo F. Schumacher, Eder J. Lenardão, and Filipe Penteado
18.1 Introduction 565
18.2 Use of Diorganyl Diselenides as a Selenium Source 566
18.3 Use of Elemental Selenium as a Selenium Source 584
18.4 Reactions Using Other Selenium Sources 600
18.5 Conclusion 604
19 Multicomponent Reactions in Isotope Labeling 613
Kevin Schofield, Aidan McMahon, Vishal Kaleeswaran, Sean Ginn, and Christopher Hulme
19.1 An Introduction to Radiotracers 613
19.2 Radiotracers and MCRs 615
19.3 Deuterium in Drug Discovery 622
20 Harnessing Multicomponent Reactions for the Functionalization of Drugs and Bioactive Natural Products via Innate Reactivity 637
Hélène Beucher and Tatiana Besset
20.1 Introduction 637
20.2 Multicomponent Reactions Involving Small Drugs and Bioactive Natural Compounds 638
20.3 Application to the Functionalization of Peptides, Proteins, and DNA 642
20.4 Conclusion 652
21 Multicomponent Reactions for the Synthesis of Protein Degraders 659
Laura Gioiello, Tracey Pirali, and Rita Maria Concetta Di Martino
21.1 Introduction on Induced Protein Degradation 659
21.2 MCRs in the Synthesis of Degraders 671
21.3 Summary and Conclusions 683
22 Synthesis of Natural Compounds via Multicomponent Reactions 689
Ana Barbero-Moreno, Miriam Ruiz, and J. Carlos Menéndez
22.1 Introduction 689
22.2 Imine-initiated MCRs 689
22.3 Isonitrile-based MCRs 696
22.4 Cycloaddition-based Multicomponent Reactions 702
22.5 Combination of Multicomponent Reactions 704
22.6 Conclusions 706
23 Multicomponent Reactions in the Total Synthesis of Biologically Active Natural Products - Part I: Reactions Based on the Use of Isocyanides, Transition Metal Catalysis, and Tandem Conjugate Addition/Electrophilic Enolate Trapping on ¿,ß-Unsaturated Carbonyls 711
Enrique L. Larghi, Andrea B. J. Bracca, Sebastián O. Simonetti, and Teodoro S. Kaufman
23.1 Introduction 711
23.2 MCRs Based on the Use of Isocyanides 711
23.3 Tandem Conjugate Addition/Electrophilic Enolate Trapping on ¿,ß-Unsaturated Carbonyl Compounds 720
23.4 MCRs Centered on Transition Metal Catalysis 725
23.5 Conclusions and Perspective 730
24 Multicomponent Reactions in the Total Synthesis of Biologically Active Natural Products - Part II: MCRs Initiated by Nucleophilic Addition to Carbonyl Compounds, Mannich and Related Reactions, Anion Relay Chemistry, [4+2]-Cycloadditions and Other Transformations 741
Enrique L. Larghi, Andrea B. J. Bracca, Sebastián O. Simonetti, and Teodoro S. Kaufman
24.1 Introduction 741
24.2 MCRs Initiated by a Nucleophilic Addition to Carbonyl Compounds 742
24.3 Three-component Mannich and Related Reactions 746
24.4 MCRs Initiated by a Nucleophilic Addition to Epoxides 753
24.5 MCRs Involving [4+2]-Cycloadditions 756
24.6 Miscellaneous MCRs 758
24.7 Conclusions and Perspective 760
25 Multicomponent Reactions in Polymer Chemistry 767
Siamak Javanbakht, Reza Mohammadi, and Ahmad Shaabani
25.1 Introduction 767
25.2 MCRs in Polymer Synthesis 768
25.3 Innovations and Applications of MCRs in Polymer Chemistry 771
25.4 Functionalization of Natural and Renewable Polymers 774
25.5 Sustainability and Green Chemistry in Multicomponent Polymer Synthesis 775
25.6 Summary and Future Outlook 778
26 Multicomponent Derivatization for Advanced Gas and Liquid Chromatographic Methods 785
Serban C. Moldoveanu and Victor David
26.1 Role of Derivatization in Chromatographic Analysis 785
26.2 Molecularity, Number of Components, and Reaction Rate Order in a Derivatization Reaction 788
26.3 Alkylation and Arylation Reactions Used for Derivatization 793
26.4 Silylation Reactions Used for Derivatization 795
26.5 Acylation and Other Similar Reactions Used for Derivatization 796
26.6 Derivatizations by Addition to Carbon-Heteroatom Multiple Bonds 800
26.7 Derivatizations with Formation of Cyclic Compounds 802
26.8 Other Derivatization Types Used in Chemical Analysis 804
26.9 Conclusions and Future Perspectives 805
27 Multicomponent Reactions in Chemical Education 809
Cristina Martini and Andrea Basso
27.1 Introduction 809
27.2 MCRs for the Synthesis of Biologically Relevant Compounds 810
27.3 Catalyzed MCRs 812
27.4 MCRs for the Generation of Molecular Complexity 817
27.5 Miscellaneous 819
27.6 Summary and Conclusions 826
References 827
Index 831