Organic Transformations in Water

Organic Transformations in Water

Principles and Applications

Ujwaldev, Sankuviruthiyil M.; Harry, Nissy Ann; Anilkumar, Gopinathan

Wiley-VCH Verlag GmbH

12/2024

384

Dura

9783527353774

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About the Editors xvii

Preface xix

List of Abbreviations xxi

1 An Introduction to Organic Transformations in Water 1
Nissy Ann Harry and Gopinathan Anilkumar

1.1 The Emergence of Water as a Solvent in Organic Chemistry 1

1.2 Green Chemistry and Water 3

1.3 Conclusion 8

References 9

2 Chemistry of "On-Water" Reactions 11
Anthony G. Coyne

2.1 Introduction 11

2.2 Broadening the Scope of On-Water Reactions 20

2.3 Conclusions 25

References 25

3 Chemistry of "In-Water" Reactions: Spotlights on Micellar and Phase-Transfer Catalysis 29
Tharique N. Ansari, Gaganpreet Kaur, Thomas J. Colacot, and Sachin Handa

3.1 Introduction 29

3.2 Understanding the Concept of Micellar Catalysis 30

3.3 Basic Principles of Phase-Transfer Catalysis 31

3.4 Highlights of Micellar Catalysis 32

3.5 Highlights of PTC 52

3.6 Conclusion 56

References 56

4 Physicochemical Aspects of "On-Water" and "In-Water" Reactions 63
Rachel Napier and Bao N. Nguyen

4.1 Introduction 63

4.2 Phase Behaviors of Realistic Reactions 64

4.3 Mechanistic Considerations 68

4.4 Green Processes Based on Water-Accelerated Reactions 79

4.5 Summary and Conclusions 80

References 80

5 C-H Activation Reactions in Aqueous Medium 83
Feng Zhou and Chao-Jun li

5.1 Introduction 83

5.2 C-H Bond Activation Reactions in Aqueous Medium 84

5.3 Summary and Conclusion 100

Acknowledgments 101

References 101

6 Recent Developments in Multicomponent Reactions in Water 105
Bibi E. M. Nanlohy and Floris P. J. T. Rutjes

6.1 Introduction 105

6.2 I-MCRs 108

6.3 Knoevenagel-Initiated MCRs 119

6.4 Summary and Conclusions 135

References 135

7 Pericyclic Reactions in Aqueous Medium 141
Surabhi Mishra, Sumran Raikwar, and Beeraiah Baire

7.1 Introduction 141

7.2 Cycloaddition Reactions in Aqueous Medium 143

7.3 Miscellaneous Cycloaddition Reactions In-Water 150

7.4 Electrocyclic Reactions In-Water (Ring Closure and Ring Opening) 154

7.5 Sigmatropic Rearrangements In-Water 156

7.6 Ene Reactions 157

7.7 Summary and Conclusions 158

References 158

8 Olefin Metathesis In-Water: Recent Progress and Challenges 165
Bengi OEzguen OEztuerk

8.1 Introduction 165

8.2 Ionic, Non-Ionic, and Amphiphilic Group-Tagged Olefin Metathesis Catalysts 166

8.3 Biopolymer Integrated Olefin Metathesis Catalysts 175

8.4 Conclusion 176

Acknowledgments 177

References 177

9 Oxidation and Reduction Reactions in Water 179
Rose Mary Philip, Padinjare Veetil Saranya, and Gopinathan Anilkumar

9.1 Introduction 179

9.2 Oxidation Reactions in Water 180

9.3 Reduction Reactions in Water 185

9.4 Summary and Conclusions 193

References 194

10 Radical Reactions in Water 197
Xiaoye Yu, Ying Zhang, and Huan-Ming Huang

10.1 Introduction 197

10.2 Transition Metal-Catalyzed Radical Reaction in Water 198

10.3 Transition Metal-Free Radical Reaction in Water 203

10.4 Photoredox Reactions Excited by Visible Light in Water 212

10.5 Conclusions 218

References 218

11 Carbene Reactions in Water 223
Xiaoye Yu, Ying Zhang, and Huan-Ming Huang

11.1 Introduction 223

11.2 Carbene Reaction in Water 223

11.3 Conclusions 228

References 229

12 Nucleophilic Addition and Substitution Reactions In-Water 231
Panackalchirayil S. Devi, Pulluparambil X. T. Rinu, and Gopinathan Anilkumar

12.1 Introduction 231

12.2 Nucleophilic Addition Reactions 232

12.3 Nucleophilic Substitution Reactions 240

12.4 Summary and Conclusions 246

References 247

13 Asymmetric Organic Reactions in Water 251
Han-Yong Bae, Woo-Hee Kim, and Seok-Ju Hong

13.1 Introduction 251

13.2 Asymmetric Metal (Lewis Acid) Catalysis in Water 252

13.3 Asymmetric Lewis Base Organocatalysis in Water 258

13.4 Asymmetric Bronsted Acid Organocatalysis in Water 261

13.5 Asymmetric Bronsted Base Organocatalysis in Water 262

13.6 Summary and Conclusions 265

Acknowledgments 266

References 266

14 Organocatalytic Reactions in Water 269
Bubun Banerjee, Anu Priya, Zsuzsanna Szalai, Aditi Sharma, Manmeet Kaur, Arvind Singh, and Gyoergy Keglevich

14.1 Introduction 269

14.2 Organocatalyzed Synthesis of Biologically Promising N-Heterocycles in Water 270

14.3 Organocatalyzed Synthesis of Biologically Promising O-Heterocycles in Water 274

14.4 Organocatalyzed Synthesis of Biologically Promising N,O-Heterocycles in Water 278

14.5 Organocatalyzed Synthesis of Biologically Promising N,S-Heterocycles in Water 279

14.6 Organocatalyzed Miscellaneous Reactions in Water 280

14.7 Asymmetric Synthesis Using Organocatalysts 283

14.8 Conclusions 288

Acknowledgments 288

References 288

15 Organic Electrocatalysis in Water 291
Samina Aslam, Sadia Rani, Kiran Lal, and Nisar Ahmed

15.1 Introduction 291

15.2 Direct vs. Mediated Reductive Oxidation and Oxidative Reduction 292

15.3 Water as a Solvent and an Electrolyte 292

15.4 Electrocatalysis 294

15.5 Water Electrolysis 295

15.6 Organic Transformations in Water: Principles and Applications 297

15.7 Benefits of Electrochemical Conversions 309

15.8 Conclusion 309

15.9 Future Perspectives 310

References 310

16 Visible Light Photocatalysis in Water 313
Camilla Russo, Francesca Brunelli, Gian Cesare Tron, and Mariateresa Giustiniano

16.1 Introduction 313

16.2 In-Water Reactions 314

16.3 On-Water Reactions 318

16.4 Photobiocatalysis 321

16.5 Summary and Conclusions 325

References 326

17 Industrial Applications of Organic Reactions in Water 329
Chitrakar Ravi and Subbarayappa Adimurthy

17.1 Introduction 329

17.2 Oxidative Esterification of Alcohols 330

17.3 Green Oxidation of Methylarenes to Benzoic Acids with Bromide/Bromate in Water 331

17.4 Environment-Friendly Synthesis of Bromoxynil and Iodoxynil 332

17.5 Synthesis of 2,6-Dibromo-4-Nitroaniline from 4-Nitroaniline in an Aqueous Medium 333

17.6 HBr-H2 O2 for Regioselective Synthesis of Bromohydrins and ?-Bromoketones and Oxidation of Benzylic/Secondary Alcohols to Carbonyl Compounds in Aqueous Medium 334

17.7 Water-Mediated Synthesis of Imidazo[1,2-a]Pyridines 336

17.8 Sulfenylation of N-Heteroarenes in Water (Rice Cooking Method) 337

17.9 Summary and Conclusions 338

Acknowledgments 339

References 339

Index 343
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Water; green solvents; green chemistry; sustainable chemistry; organic synthesis, catalysis; on-water; in-water; phase-transfer catalysis; micellar catalysis; multicomponent reactions; pericyclic reactions; olefin metathesis; C-H activation; oxidation; reduction; radical reaction; carbene reaction; nucleophilic addition; nucleophilic substitution; asymmetric synthesis; organocatalysis; electrocatalysis; visible light photocatalysis; industrial applications