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Practical Functional Group Synthesis

ISBN: 978-1-119-01577-2
704 pages
March 2016
Practical Functional Group Synthesis (1119015774) cover image

Description

A practical handbook for chemists performing bond forming reactions, this book features useful information on the synthesis of common functional groups in organic chemistry.

• Details modern functional group synthesis through carbon-heteroelement (N, O, P, S, B, halogen) bond forming reactions with a focus on operational simplicity and sustainability.
• Summarizes key and recent developments – which are otherwise scattered across journal literature – into a single source
• Contains over 100 detailed preparations of common functional groups
• Included 25 troubleshooting guides with suggestions and potential solutions to common problems.
• Complements the text in enhanced ebook editions with tutorial videos where the author provides an introduction to microwave assisted chemistry

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Table of Contents

Preface ix

Acknowledgments xi

1 Introduction to Practical Functional Group Synthesis 1

1.1 General Approaches for Designing Syntheses 1

1.2 New Versions of “Classic” Organic Reactions 6

1.3 Solvent Selection and Solvent‐Free Reactions 7

1.4 Operational Simplicity 11

1.5 Metal‐Catalyzed Transformations 12

1.6 Organocatalysis 16

1.7 Microwave‐ and Ultrasound‐Assisted Chemistry 17

1.8 Sustainability 25

1.9 Asymmetric Synthesis 32

References 33

2 Preparation of Alcohols, Ethers, and Related Compounds 37

2.1 Preparation of Alcohols, Ethers, and Related Compounds through the Formation of Oxygen–Carbon(sp3) Bonds 37

2.2 Preparation of Phenols, Aryl Ethers, and Related Compounds


 through the Formation of Oxygen–Carbon(sp2) Bonds 57

2.3 Preparation of Vinyl Ethers and Related Compounds through the Formation of Oxygen–Carbon(sp2) Bonds 84

2.4 Preparation of Alkynyl Ethers and Related Compounds through the Formation of Oxygen–Carbon(sp) Bonds 114

References 117

3 Synthesis of Amines, Amides, and Related Compounds 123

Alkylamines 123

3.1 Synthesis of Alkylamines and Related Compounds through Nitrogen–Carbon(sp3) Bond‐Forming Reactions 123

3.2 Synthesis of Arylamines and Related Compounds through Nitrogen–Carbon(sp2) Bond‐Forming Reactions 150

3.3 Synthesis of Vinylamines and Related Compounds through Nitrogen–Carbon(sp2) Bond‐Forming Reactions 191

3.4 Synthesis of Ynamides and Related Compounds through Nitrogen–Carbon(sp) Bond‐Forming Reactions 207

References 213

4 Synthesis of Organophosphines, Phosphonates, and Related Compounds 219

4.1 Introduction to the Synthesis of Organophosphorus Compounds Generated through the Formation of Phosphorus–Carbon Bonds 219

4.2 Synthesis of Alkylphosphines and Related Compounds through the Formation of Phosphorus–Carbon(sp3) Bonds 220

4.3 Synthesis of Arylphosphines and Related Compounds through the Formation of Phosphorus–Carbon(sp2) Bonds 338

4.4 Synthesis of Vinylphosphines and Related Compounds through the Formation of Phosphorus–Carbon(sp2) Bonds 398

4.5 Synthesis of Alkynylphosphines and Related Compounds through the Formation of Phosphorus–Carbon(sp) Bonds 441

References 454

5 Synthesis of Thioethers, Sulfones, and Related Compounds 471

5.1 Synthesis of Thioethers and Related Compounds through the Formation of Sulfur–Carbon(sp3) Bonds 471

5.2 Synthesis of Aryl Thioethers and Related Compounds through the Formation of Sulfur–Carbon(sp2) Bonds 481

5.3 Synthesis of Vinyl Thioethers and Related Compounds through the Formation of Sulfur–Carbon(sp2) Bonds 498

5.4 Synthesis of Thioethers and Related Compounds through the Formation of Sulfur–Carbon(sp) Bonds 506

References 510

6 Synthesis of Organoboronic Acids, Organoboronates, and Related Compounds 515

6.1 Synthesis of Alkylboronates and Related Compounds through the Formation of Boron–Carbon(sp3) Bonds 515

6.2 Synthesis of Arylboronates and Related Compounds through the Formation of Boron–Carbon(sp2) Bonds 526

6.3 Synthesis of Vinylboronates and Related Compounds


 through the Formation of Boron–Carbon(sp2) Bonds 538

6.4 Synthesis of Alkynylboronates and Related Compounds through the Formation of Boron–Carbon(sp) Bonds 549

References 552

7 Synthesis of Organohalides 557

7.1 Synthesis of Alkyl Halides through the Formation of Halogen–Carbon(sp3) Bonds 557

7.2 Synthesis of Aryl Halides through the Formation of Halogen–Carbon(sp2) Bonds 590

7.3 Synthesis of Vinyl Halides through the Formation of Halogen–Carbon(sp2) Bonds 628

7.4 Synthesis of Alkynyl Halides through the Formation of Halogen–Carbon(sp) Bonds 655

References 670

Index 679

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Author Information

Robert A. Stockland, Jr., PhD, is a Professor of Chemistry at Bucknell University where he teaches organic and inorganic chemistry. His research interests are focused on the development of new synthetic methodology leading to the preparation of new compounds and challenging linkages. In addition to reporting the synthesis of over 200 new compounds, Dr. Stockland has authored a book chapter on sustainable organic reactions and co-edited a symposium book on NMR spectroscopy.
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