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
