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Organic Chemistry: Breakthroughs and Perspectives

Kuiling Ding (Editor), Li-Xin Dai (Editor)
ISBN: 978-3-527-32963-2
853 pages
September 2012
Organic Chemistry: Breakthroughs and Perspectives (3527329633) cover image
This helpful, useful, practical book presents the most important achievements in organic chemistry over the past decade, summarizing such major developments as C-H activation, organocatalysis, and supramolecular chemistry. Each chapter contains two or three personal, hitherto unpublished, commentaries by leading experts on the topic. This reference work focuses on four main areas: the total synthesis of natural products and chemical biology; synthetic methodology; physical organic chemistry and chemistry relevant to meeting the urgent needs of humanity. The result is a complete and extremely useful source of a wide variety of information for graduate students, post-docs and researchers.
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List of Contributors XXIII

Introduction XXXV

1 Diversity-Oriented Syntheses of Natural Products and Natural Product-Like Compounds 1
Ling-Min Xu, Yu-Fan Liang, Qin-Da Ye, and Zhen Yang

1.1 Introduction 1

1.2 Diversity-Oriented Synthesis (DOS) 2

1.3 Diverted Total Synthesis (DTS) 7

1.4 Function-Oriented Synthesis (FOS) 9

1.5 Target-Oriented Synthesis (TOS) 11

1.6 Conclusion and Perspectives 24

Acknowledgments 26

References 26

Commentary Part 28

Comment 1 28
Michael Foley

Comment 2 29
Scott A. Snyder

Comment 3 30
Da-Wei Ma

Authors’ Response to the Commentaries 31

References 31

2 Total Synthesis of Natural Products and the Synergy with Synthetic Methodology 33
Qian Wang and Jie-Ping Zhu

2.1 Introduction 33

2.2 Domino Process 36

2.3 Multicomponent Reactions 43

2.4 Oxidative Anion Coupling 52

2.5 Pattern Recognition 60

2.6 Conformation-Directed Cyclization 65

2.7 Conclusion and Perspectives 69

Acknowledgments 70

References 70

Commentary Part 72

Comment 1 72
Kyriacos C. Nicolaou

Comment 2 73
Henry N.C. Wong

Comment 3 75
Wei-Dong Li

References 77

3 Interplay Between the Chemical Space and the Biological Space 81
Ren-Xiao Wang

3.1 Chemical Biology: Historical and Philosophical Aspects 81

3.2 Preparation of Chemical Libraries 90

3.3 Screening Strategies 95

3.4 Target Elucidation and Validation 106

3.5 Conclusion and Perspectives 116

References 117

Commentary Part 121

Comment 1 121
Ke Ding

Comment 2 121
Li-He Zhang

Comment 3 122
Jun-Ying Yuan

Author’s Response to the Commentaries 122

References 123

4 Biosynthesis of Pharmaceutical Natural Products and Their Pathway Engineering 125
Michael J. Smanski, Xu-Dong Qu, Wen Liu, and Ben Shen

4.1 Introduction 125

4.2 Expanded Paradigms in Biosynthetic Logic 126

4.3 New Approaches to NP Biosynthesis Research 147

4.4 Better Understanding of the Scope and Diversity of NP Production 156

4.5 Future Perspectives 168

Acknowledgments 170

Abbreviations 171

References 171

Commentary Part 178

Comment 1 178
Yi Tang

Comment 2 178
Yi Yu and Zi-Xin Deng

Authors’ Response to the Commentaries 179

Response to Yi Tang 179

Response to Yi Yu and Zixin Deng 179

5 Carbohydrate Synthesis Towards Glycobiology 181
Biao Yu and Lai-Xi Wang

5.1 Introduction 181

5.2 Advances in Chemical Glycosylation 182

5.3 New Strategies in Oligosaccharide Assembly 189

5.4 Enzymatic and Chemoenzymatic Methods 193

5.5 Synthesis of Heparin and Heparan Sulfate Oligosaccharides 195

5.6 Synthesis of Homogeneous Glycoproteins 200

5.7 Synthesis of Carbohydrate-Containing Complex Natural Compounds 206

5.8 Conclusion and Perspectives 212

Acknowledgments 212

References 212

Commentary Part 218

Comment 1 218
Sam Danishefsky

Comment 2 218
David Crich

Authors’ Response to the Commentaries 219

References 219

6 Chemical Synthesis of Proteins 221
Lei Liu

6.1 Introduction 221

6.2 Brief History 222

6.3 Current Technology 227

6.4 Applications 236

6.5 Conclusion and Perspectives 242

References 242

Commentary Part 244

Comment 1 244
Sam Danishefsky

Comment 2 244
David Crich

References 245

7 CuAAC: the Quintessential Click Reaction 247
Valery V. Fokin

7.1 Introduction 247

7.2 Azide–Alkyne Cycloaddition: the Basics 249

7.3 CuAAC: Catalysts and Ligands 251

7.4 Mechanistic Aspects of the CuAAC 258

7.5 Reactions of 1-Iodoalkynes 264

7.6 Examples of Application of the CuAAC Reaction 266

7.7 Reactions of Sulfonyl Azides 269

7.8 Outlook/Perspective 273

Acknowledgments 273

References 273

Commentary Part 276

Comment 1 276
Krzysztof Matyjaszewski

References 276

8 Transition Metal-Catalyzed C–H Functionalization: Synthetically Enabling Reactions for Building Molecular Complexity 279
Keary M. Engle and Jin-Quan Yu

8.1 Introduction 279

8.2 Background and Early Work 281

8.3 First Functionalization: Challenges in Hydrocarbon Chemistry 293

8.4 Further Functionalization: C–H Bonds as Reaction Partners in Organic Synthesis 300

8.5 Catalytic C–H Functionalization via Metal Insertion 303

8.6 Other Emerging Metal-Catalyzed Further Functionalization Methods 311

8.7 Outlook and Conclusion 321

Acknowledgments 322

Abbreviations 322

References 323

Commentary Part 328

Comment 1 328
Huw M.L. Davies

Comment 2 329
Zhenfeng Xi

Comment 3 330
Shu-Li You

Comment 4 332
Zhang-Jie Shi

Authors’ Response to the Commentaries 333

References 333

9 An Overview of Recent Developments in Metal-Catalyzed Asymmetric Transformations 335
Christian A. Sandoval and Ryoji Noyori

9.1 Introduction 335

9.2 Asymmetric Carbon–Carbon Bond Formation 336

9.3 Asymmetric Reductions and Oxidations 348

9.4 Conclusion 353

References 353

Commentary Part 363

Comment 1 363
Qi-Lin Zhou

Comment 2 363
Andreas Pfaltz

Comment 3 365
Xue-Long Hou

Comment 4 365
Hisashi Yamamoto

References 366

10 The Proline-Catalyzed Mannich Reaction and the Advent of Enamine Catalysis 367
Benjamin List and Sai-Hu Liao

10.1 Introduction 367

10.2 The Proline-Catalyzed Mannich Reaction 367

10.3 Conclusion 374

References 374

Commentary Part 375

Comment 1 375
Seiji Shirakawa and Keiji Maruoka

Comment 2 377
The Early Status of Asymmetric Organocatalysis 377

Liu-Zhu Gong

Milestone in Asymmetric Organocatalysis 378

Enamine Catalysis 378

Iminium Catalysis 378

Domino Reactions by Amine Catalysis 378

Hydrogen Bonding Catalysis 378

Conclusion 379

Comment 3 379
Wen-Jing Xiao

References 382

11 Recent Topics in Cooperative Catalysis: Asymmetric Catalysis, Polymerization, Hydrogen Activation, and Water Splitting 385
Motomu Kanai

11.1 Introduction 385

11.2 Cooperative Catalysis in Asymmetric Reactions 387

11.3 Cooperative Catalysis in Alkene Polymerization 393

11.4 Cooperative Catalysis in Hydrogen Activation/Generation 394

11.5 Conclusion and Perspectives 398

References 398

Commentary Part 401

Comment 1 401
Takao Ikariya

Comment 2 402
Takashi Ooi

Comment 3 405
Kuiling Ding

Comment 4 409
David Milstein

Authors’ Response to the Commentaries 410

References 411

12 Flourishing Frontiers in Organofluorine Chemistry 413
G. K. Surya Prakash and Fang Wang

12.1 Introduction 413

12.2 Synthetic Approaches for the Introduction of Fluorine-Containing Functionalities and Related Chemistry 415

12.3 Conclusion and Perspectives 459

Acknowledgment 460

References 460

Commentary Part 470

Comment 1 470
David O’Hagan

Comment 2 471
Jinbo Hu

Comment 3 472
Kuiling Ding and Li-Xin Dai

Authors’ Response to the Commentaries 472

References 473

Addendum 473

13 Supramolecular Organic Chemistry: the Foldamer Approach 477
Zhan-Ting Li

13.1 Introduction 477

13.2 Foldamers: the Background 479

13.3 Molecular Recognition 480

13.4 Homoduplex 497

13.5 Organogels 499

13.6 Vesicles 501

13.7 Supramolecular Liquid Crystals 502

13.8 Macrocycles 503

13.9 Catalysis 510

13.10 Macromolecular Self-Assembly 514

13.11 Conclusion and Perspectives 516

Acknowledgments 517

References 517

Commentary Part 520

Comment 1 520
Peter J. Stang

Comment 2 521
Liang Zhao and Mei-Xiang Wang

Introduction 521

Macrocyclic Compounds 522

Cycloparaphenylenes 522

Pillar[n]arenes 524

Heteracalixaromatics 525

Noncovalent Interactions 527

Quadruple Hydrogen Bonding 527

Halogen Bonding 528

Anion–π Interaction 529

Perspectives 530

Acknowledgements 531

Comment 3 531
Chen-Ho Tung

Author’s Response to the Commentaries 532

Reply to Zhao and Wang’s Comments 532

Reply to Tung’s Comments 533

Reply to Stang’s Comments 533

References 533

14 Novel Catalysis for Alkene Polymerization Mediated by Post-Metallocenes: a Gateway to New Polyalkenes 537
Hiromu Kaneyoshi, Haruyuki Makio, and Terunori Fujita

14.1 Introduction 537

14.2 Late Transition Metal Complexes 538

14.3 Early Transition Metal Complexes 544

14.3.1 Phenoxyimine-Ligated Group 4 Metal Complexes 544

14.4 Conclusion and Perspectives 553

Acknowledgment 554

References 554

Commentary Part 555

Comment 1 555
Robert Grubbs

Comment 2 556
Jun Okuda

General 556

Early Work on Late Metals 556

Ligand Design Principles for Post-metallocenes 556

Comment 3 557
Eugene Y.-X. Chen

Authors’ Response to the Commentaries 559

References 559

15 Chem Is Try Computationally and Experimentally: How Will Computational Organic Chemistry Impact Organic Theories, Mechanisms, and Synthesis in the Twenty-First Century? 561
Zhi-Xiang Yu and Yong Liang

15.1 Introduction 561

15.2 Developing New Theories, Concepts, and Understandings for Organic Chemistry 561

15.3 Understanding Reaction Mechanisms 571

15.4 Computation-Guided Development of New Catalysts, New Reactions, and Synthesis Planning for Ideal Synthesis 583

15.5 Conclusion 595

Acknowledgments 597

References 597

Commentary Part 600

Comment 1 600
K. N. Houk

Comment 2 600
Yun-Dong Wu and Xin-Hao Zhang

References 601

16 Case Study of Mechanisms in Synthetic Reactions 603
Ai-Wen Lei and Li-Qun Jin

16.1 Introduction 603

16.2 Mechanistic Study of Coupling Reactions 604

16.3 Mechanistic Study of Aerobic Oxidation 627

16.4 Conclusion and Perspective 634

Acknowledgments 635

References 635

Commentary Part 638

Comment 1 638
Xin Mu, Guo-Sheng Liu, and Qi-Long Shen

Comment 2 640
Yoshinori Yamamoto

Authors’ Response to the Commentaries 640

References 640

17 Organic Materials and Chemistry for Bulk Heterojunction Solar Cells 643
Chun-Hui Duan, Fei Huang, and Yong Cao

17.1 Introduction 643

17.2 Molecular Design and Engineering of Donor Materials 645

17.3 Molecular Design and Engineering of Acceptor Materials 662

17.4 Conclusion and Outlook 671

Acknowledgments 671

References 671

Commentary Part 676

Comment 1 676
Niyazi Serdar Sariciftci

Comment 2 677
Yongfang Li

Comment 3 681
Guillermo C. Bazan

Comment 4 682
Xiong Gong

Authors’ Response to the Commentaries 682

References 682

18 Catalytic Utilization of Carbon Dioxide: Actual Status and Perspectives 685
Albert Boddien, Felix G¨artner, Christopher Federsel, Irene Piras, Henrik Junge, Ralf Jackstell, and Matthias Beller

18.1 Introduction 685

18.2 Catalytic Reductions of CO2 to Formic Acid and Methanol 686

18.3 CO2 as a C1-Building Block in C–C Coupling Reactions 702

18.4 Catalytic C–O Bond Formation Utilizing Carbon Dioxide 703

18.5 Current Industrial Processes Using CO2 710

18.6 Conclusion and Outlook 715

References 716

Commentary Part 722

Comment 1 722
Gábor Laurenczy

Comment 2 723
Min Shi

References 724

19 Synthetic Chemistry with an Eye on Future Sustainability 725
Guo-Jun Deng and Chao-Jun Li

19.1 Introduction 725

19.2 Cross-Dehydrogenative Coupling 729

19.3 Nucleophilic Addition of Terminal Alkynes in Water 741

19.4 Conclusion and Perspectives 749

Acknowledgments 750

References 750

Commentary Part 754

Comment 1 754
Roger A. Sheldon

Comment 2 756
Tak Hang Chan

References 758

20 Organic π-Conjugated Molecules for Organic Semiconductors and Photovoltaic Materials 759
De-Qing Zhang, Xiao-Wei Zhan, Zhao-Hui Wang, Jian Pei, Guan-Xin Zhang, and Dao-Ben Zhu

20.1 Introduction 759

20.2 Conjugated Molecules for p-Type Organic Semiconductors 760

20.3 Conjugated Molecules for n-Type Organic Semiconductors 766

20.4 Conjugated Molecules for Photovoltaic Materials 769

20.5 Conclusion and Outlook 773

References 774

Commentary Part 777

Comment 1 777
Seth R. Marder

Comment 2 777
Tien Yau Luh

Authors’ Response to the Commentaries 779

References 779

21 The Future of Organic Chemistry–an Essay 781
Ronald Breslow

21.1 Introduction 781

21.2 The Field of Organic Chemistry Will Broaden 781

21.3 Conclusion 789

Index 791

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Kuiling Ding received his B.S. degree from Zhengzhou University (1985) and a Ph.D. from Nanjing University (1990). He was a faculty member of Zhengzhou University from 1990 to 1998. He was engaged in postdoctoral research at Ryukoku University during 1993-1994. He spent another year at TIT as a UNESCO research fellow before joined the faculty of the Shanghai Institute of Organic Chemistry (SIOC) in 1999, where he is currently a professor of organic chemistry and director of SIOC. His research interests include the development of new methodologies and chiral catalysts for asymmetric reactions. Professor Ding has co-authored over 100 scientific publications and fourteen patents. He has also received numerous scientific awards, including the National Natural Science Award of China, Shanghai Peony Award for Natural Science and Eli Lilly Scientific Excellence Award in Chemistry. He is currently serving the International Advisory Board of several journals including Eur. J. Org. Chem, Asian J. Org. Chem., Chem. Commun., Adv. Synth. Cat., Curr. Org. Synth. and ChemPlusChem., as well as the editorial board of Catal. Sci. Tech.

Li-Xin Dai is Professor at the Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences. He graduated from Zhejiang University in 1947 and joined the SIOC in 1953. He is the Honorary President of Shanghai Society of Chemistry and Chemical Industry,
the Academic Committee Board Member of SIOC and the Honorary Board Member of Asian Journal of Organic Chemistry. His research interests include the design of chiral ligands and their applications in asymmetric catalysis. He was elected as the Member of the
Chinese Academy of Sciences in 1993. He has co-authored over 150 scientific publications and has received numerous scientific awards, including Ho Leung Ho Lee Prize and the National Natural Science Award of China.
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“This volume, though oriented primarily to major developments in synthesis and chemical biology, with relatively little attention to topics in physical organic chemistry such as nonclassical carbocations, is a valuable resource for all academic and professional chemistry collections. Summing Up: Highly recommended. Lower-division undergraduates and above."  (Choice, 1 July 2013)

 

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