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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 �zgün �ztürk
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 Brønsted Acid Organocatalysis in Water 261
13.5 Asymmetric Brønsted 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 György 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 α-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