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Green Solvents, Volume 5 Reactions in Water

by: Anastas, Paul T.; Li, Chao-Jun

Green Solvents, Volume 5 Reactions in Water

by: Anastas, Paul T.; Li, Chao-Jun

ISBN 13:
9783527325917
ISBN 10:
3527325913
Edition: 1st
Format: Hardcover
Copyright: 09/30/2013
Publisher: Wiley-VCH

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Green Solvents, Volume 5 Reactions in Water > ISBN13: 9783527325917

Summary

The shift towards being as environmentally-friendly as possible has resulted in the need for this important volume on the topic of reactions in water. Edited by one of the leaders in the field, Professor C.-J. Li, this is an essential resource for anyone wishing to gain an understanding of the world of green chemistry, as well as for chemists, environmental agencies and chemical engineers.

Author Biography

Paul T. Anastas joined Yale University as Professor and iserves as the Director of the Center for Green Chemistry and Green Engineering at Yale. From 2004-2006, Paul Anastas has been the Director of the Green Chemistry Institute in Washington, D.C. Until June of 2004 he served as Assistant Director for Environment at e White House Office of Science and Technology Policy where his responsibilities included a wide range of environmental science issues including furthering international public-private cooperation in areas of Science for Sustainability such as Green Chemistry. In 1991, he established the industry-government-university partnership Green Chemistry Program, which was expanded to include basic research, and the Presidential Green Chemistry Challenge Awards. He has published and edited several books in the field of Green Chemistry and developed the 12 principles of Green Chemistry.

About the Editors XIII

List of Contributors XV

1 The Principles of and Reasons for Using Water as a Solvent for Green Chemistry 1
Ronald Breslow

1.1 Introduction 1

1.2 Binding of Two Species Together Driven by the Hydrophobic Effect in Water 2

1.3 Aromatic Chlorination 3

1.4 Acylation of Cyclodextrins by a Bound Ester 4

1.5 Mimics of Metalloenzymes Using the Hydrophobic Effect in Water 5

1.6 Mimics of the Enzyme Ribonuclease 7

1.7 Mimics of Enzymes that Use Pyridoxamine Phosphate and Pyridoxal Phosphate as Coenzymes 9

1.8 Artificial Enzymes Carrying Mimics of Thiamine Pyrophosphate 15

1.9 Enolizations and Aldol Condensations 17

1.10 Hydrophobic Acceleration of Diels–Alder Reactions 18

1.11 Selectivities in Water Induced by the Hydrophobic Effect – Carbonyl Reductions 18

1.12 Selectivities in Water Induced by the Hydrophobic Effect – Oxidations 19

1.13 Using Hydrophobic Effects in Water to Determine the Geometries of Transition States for Some Important
Reactions 21

1.14 Conclusion 25

References 25

2 Green Acid Catalysis in Water 31
Chikako Ogawa and Sh_u Kobayashi

2.1 Introduction 31

2.2 Lewis Acids in Water 31

2.3 Chiral Lewis Acid-catalyzed Asymmetric Reactions in Water 36

2.4 Brønsted Acid Catalysis in Pure Water 45

2.5 Conclusion and Perspective 53

References 53

3 Green Bases in Water 57
José M. Fraile, Clara I. Herrerías, and José A. Mayoral

3.1 Introduction 57

3.2 Types of Bases and Their Use from a Green Point of View 58

3.3 Liquid–Liquid Processes 59

3.4 Solid–Liquid Processes 65

References 70

4 Green Oxidation in Water 75
Roger A. Sheldon

4.1 Introduction 75

4.2 Water-soluble Ligands 76

4.3 Oxidations Catalyzed by Metalloporphyrins and Metallophthalocyanines 76

4.4 Epoxidation and Dihydroxylation of Olefins in Aqueous Media 78

4.5 Alcohol Oxidations in Aqueous Media 85

4.6 Aldehyde and Ketone Oxidations in Water 94

4.7 Sulfoxidations in Water 96

4.8 Conclusion 97

References 98

5 Green Reduction in Water 105
Xiaofeng Wu and Jianliang Xiao

5.1 Introduction 105

5.2 Water-soluble Ligands 106

5.3 Hydrogenation in Water 108

5.4 Transfer Hydrogenation in Water 123

5.5 Role of Water 137

5.6 Conclusion 142

References 142

6 Coupling Reactions in Water 151
Lucie Leseurre, Jean-Pierre Genêt, and Véronique Michelet

6.1 Introduction 151

6.2 Reaction of Carbonyl Compounds and Derivatives 151

6.3 Reaction of Alkenes and Alkynes 163

6.4 Reaction of Organic Halides and Derivatives 172

6.5 Conclusion 191

References 191

7 .On Water. for Green Chemistry 207
Li Liu and Dong Wang

7.1 Introduction 207

7.2 Pericyclic Reactions 208

7.3 Addition of Heteronucleophiles to Unsaturated Carbonyl Compounds 211

7.4 Enantioselective Direct Aldol Reactions 213

7.5 Coupling Reactions 215

7.6 Oxidation 221

7.7 Bromination Reactions 223

7.8 Miscellaneous Reactions 224

7.9 Theoretical Studies 226

7.10 Conclusion 227

References 227

8 Pericyclic Reactions in Water. Towards Green Chemistry 229
Jaap E. Klijn and Jan B.F.N. Engberts

8.1 Introduction 229

8.2 Pericyclic Reactions in Aqueous Media 234

8.3 Conclusion 267

References 268

9 Non-conventional Energy Sources for Green Synthesis in Water (Microwave, Ultrasound, and Photo) 273
Vivek Polshettiwar and Rajender S. Varma

9.1 Introduction 273

9.2 MW-assisted Organic Transformations in Aqueous Media 274

9.3 Sonochemical Organic Transformations in Aqueous Media 285

9.4 Photochemical Transformations in Aqueous Media 287

9.5 Conclusion 288

References 288

10 Functionalization of Carbohydrates in Water 291
Marie-Christine Scherrmann, André Lubineau, and Yves Queneau

10.1 Introduction 291

10.2 C–C Bond Formation Reactions 292

10.3 C–N Bond Formation Reactions 309

10.4 Functionalization of Hydroxy Groups 312

10.5 Glyco-organic Substrates and Reactions in Aqueous Sugar Solutions 319

10.6 Conclusion 324

References 324

11 Water Under Extreme Conditions for Green Chemistry 331
Phillip E. Savage and Natalie A. Rebacz

11.1 Introduction 331

11.2 Background 332

11.3 Recent Progress in HTW Synthesis 343

12 Water as a Green Solvent for Pharmaceutical Applications 363
Peter Dunn

12.1 Introduction – Is Water a Green Solvent? 363

12.2 Water-based Enzymatic Processes 363

12.3 Processes in Which the Product is Isolated by pH Adjustment to the Isoelectric Point 374

12.4 Carbon–Carbon Bond-forming Cross-coupling Reactions in Water 375

12.5 Pharmaceutical Processes Using Mixed Aqueous Solvents 378

12.6 Conclusion 380

References 382

13 Water as a Green Solvent for Bulk Chemicals 385
Ferenc Joó and Ágnes Kathó

13.1 Introduction 385

13.2 Hydroformylation – an Overview 386

13.3 Water as Solvent for Hydroformylation 393

13.4 Water as Solvent in the Production of 2,7-Octadien–1-ol (Kuraray Process) 403

13.5 Conclusion 405

References 406

Index 409

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