Practical Functional Group Synthesis

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