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Efficient Hydrocarbon Reactions in Organic Synthesis

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Addition Reactions with Unsaturated Hydrocarbons

Provides comprehensive coverage of the atom-economic approach to functionalized molecules using unsaturated hydrocarbons as starting materials

Unsaturated hydrocarbons have emerged as an important class of fundamental starting materials in organic synthesis. Synthetic methodologies incorporating unsaturated hydrocarbons continue to expand due to their numerous applications in the synthesis of a vast array of chemicals.

Addition Reactions with Unsaturated Hydrocarbons presents an up-to-date overview of modern methods that utilize reactions of unsaturated hydrocarbons as building blocks of organic synthesis, covering the conceptual and practical knowledge required for designing atom-efficient reactions to synthesize functionalized molecules. This authoritative volume discusses homo-dimerization and cross-dimerization of alkynes and/or alkenes, synthesis of carbonyl compounds from the hydration of alkynes, cycloadditions of alkynes and alkenes for the synthesis of carbocycles and heterocycles, double functionalization of alkynes and alkenes by addition reactions of element-element bonds, and more.

  • Summarizes the most recent developments in the reactions of unsaturated hydrocarbons
  • Features more than 600 schemes describing typical reactions starting from unsaturated hydrocarbons
  • Covers topics such as alkynylated reactions, addition and cycloaddition reactions of alkynes and alkenes, and carbonylation of alkynes and alkenes with carbon monoxide
  • Includes examples of synthesis procedures of natural products involving alkyne transformation

With comprehensive coverage of important reactions of unsaturated hydrocarbons, Addition Reactions with Unsaturated Hydrocarbons is a valuable resource for organic chemists, pharmaceutical chemists, and biochemists in both academia and industry as well as an excellent reference text for graduate students in relevant areas of chemistry.

Author(s): Ruimao Hua
Publisher: Wiley-VCH
Year: 2022

Language: English
Pages: 449
City: Weinheim

Cover
Title Page
Copyright
Contents
Preface
Acknowledgments
Abbreviations
Chapter 1 Dimerization of Alkynes and Alkenes
1.1 Markovnikov Dimerization of Terminal Alkynes
1.2 Anti‐Markovnikov (Head‐to‐Head) Dimerization of Terminal Alkynes
1.3 Dimerization and Cross‐dimerization of Terminal Alkenes
1.4 Cross‐dimerization of Different Alkynes or Alkynes with Alkenes
References
Chapter 2 Addition of C(sp)H Bonds to Unsaturated Compounds
2.1 Addition of Terminal Alkynes to Carbonyl Compounds
2.2 Addition of Terminal Alkynes to Alkenes
2.3 Addition of Terminal Alkynes to Imines
2.4 Addition of Terminal Alkynes to Other Compounds
References
Chapter 3 Functionalized Alkenes from Hydrofunctionalization of Alkynes
3.1 Hydroborations of Alkynes
3.2 Hydrosilylation of Alkynes
3.3 Hydrostannation of Alkynes
3.4 Hydroamination of Alkynes
3.4.1 Hydroamination of Alkynes with Primary Amines
3.4.2 Hydroamination of Alkynes with Secondary Amines
3.4.3 Cyclohydroamination of Alkynes
3.4.4 Aminocarbonylation of Alkynes
3.5 Hydrophosphination of Alkynes and Related HP(O) Addition
3.5.1 Hydrophosphination of Alkynes
3.5.2 Addition of PV(O)H Bond to Alkynes
3.6 Hydrothiolation of Alkynes
3.6.1 Markovnikov Hydrothiolation of Alkynes
3.6.2 Anti‐Markovnikov Hydrothiolation of Alkynes
3.7 Addition of O‐nucleophiles to Alkynes
3.7.1 Addition of Alcohols and Phenols to Alkynes
3.7.2 Addition of Acids to Alkynes
References
Chapter 4 Hydrofunctionalization of Carbon–Carbon Double Bonds
4.1 Hydroboration of Alkenes
4.1.1 Markovnikov Hydroboration of Alkenes
4.1.2 Anti‐Markovnikov Hydroboration of Alkenes
4.1.3 Hydroboration of Allenes and 1,3‐dienes
4.1.4 Asymmetric Hydroboration of Alkenes
4.2 Hydrosilylation of Carbon–Carbon Double Bonds
4.2.1 Markovnikov and Anti‐Markovnikov Hydrosilylation of Alkenes
4.2.2 Hydrosilylation of Allenes
4.2.3 Hydrosilylation of 1,3‐dienes
4.2.4 Asymmetric Hydrosilylation of Alkenes
4.3 Hydrostannation of Carbon–Carbon Double Bonds
4.4 Hydroamination of Carbon–Carbon Double Bonds
4.4.1 Markovnikov Hydroamination of Alkenes
4.4.2 Anti‐Markovnikov Hydroamination of Alkenes
4.4.3 Hydroamination of Allenes and 1,3‐dienes
4.4.4 Asymmetric Hydroamination of Alkenes
4.4.5 Nitrogen Heterocycles from Intramolecular Hydroamination of Alkenes
4.5 Hydrophosphination of Alkenes and Related PV(O)H Addition
4.6 Hydrothiolation of Carbon–Carbon Double Bonds
4.7 Addition of O‐nucleophiles to Alkenes
References
Chapter 5 Double Functionalization of Alkynes and Alkenes by Addition of Element–Element Bonds
5.1 Addition Reaction of Group 13 Element–Element Bonds
5.1.1 cis‐Addition Reactions to Alkynes
5.1.2 trans‐Addition Reactions to Alkynes
5.1.3 Addition Reactions to Alkenes
5.1.4 Synthesis of 1,1‐diborylalkanes/Alkenes via Addition of BB Bond
5.2 Addition Reaction of Group 14 Element–Element Bonds
5.3 Addition Reaction of Group 15 Element–Element Bond
5.4 Addition Reactions of Group 16 Element–Element Bond
5.4.1 cis‐Addition Reactions to Alkynes
5.4.2 trans‐Addition Reactions to Alkynes
5.4.3 Different Heteroatom Bond Addition Reactions to Alkynes
5.4.4 Addition Reactions to Alkenes
5.5 Addition Reactions of Element–Element Bonds from Different Group Heteroatoms
5.5.1 cis‐Addition Reactions to Alkynes
5.5.2 trans‐Addition Reactions to Alkynes
5.5.3 Addition Reactions to Alkenes
References
Chapter 6 Double Functionalization of Alkynes by Addition of Carbon–Element Bonds
6.1 Addition Reactions of Carbon–Group 13 Bonds
6.2 Addition Reactions of Carbon–Group 14 Bonds
6.2.1 Addition Reactions of Carbon–Silicon Bonds
6.2.2 Addition Reactions of Carbon–Germanium Bonds
6.2.3 Addition Reactions of Carbon–Tin Bonds
6.3 Addition Reactions of Carbon–Group 15 Bonds
6.4 Addition Reactions of Carbon–Group 16 Bonds
6.4.1 Addition Reactions of Carbon–Oxygen Bonds
6.4.2 Addition Reaction of Carbon–Sulfur Bonds
6.4.3 Addition Reactions of Carbon–Selenium Bonds
6.5 Addition Reactions of Carbon–Halogen Bonds to Alkynes
6.5.1 C(sp3)X Activation and Its Addition Reactions
6.5.2 C(sp2)X Activation and Its Addition Reactions
6.5.3 C(sp)X Activation and Its Addition Reactions
6.6 Addition Reactions of Carbon–Carbon Single Bonds
6.6.1 Addition Reactions of Strained CC Bonds
6.6.2 Addition Reactions of CCN Bonds
6.6.3 Other Carbon–Carbon Bond Cleavage and Their Addition Reactions
References
Chapter 7 Carbocycles from Annulation of Alkynes and Alkenes
7.1 Four‐Membered Carbocycles
7.1.1 Construction of Cyclobutenes
7.1.2 Construction of Cyclobutanes
7.2 Five‐Membered Carbocycles
7.2.1 Five‐Membered Carbocycles by [2 + 2 + 1] Cycloaddition
7.2.2 Five‐Membered Carbocycles by [3 + 2] Cycloaddition
7.2.3 Intramolecular Cycloaddition of Active sp3 CH to Carbon–Carbon Unsaturated Bonds
7.2.4 Five‐Membered Carbocycles from Intramolecular Cycloaddition of Unsaturated Bonds
7.3 Six‐Membered Carbocycles
7.3.1 Benzene Ring Formation
7.3.2 Naphthalene and Polyaromatic Hydrocarbons (PAHs) Ring Formation
7.3.3 1,3‐Cyclohexadiene Ring Formation Via Cycloaddition of Alkynes
7.4 Seven‐Membered Carbocycles
7.5 Eight‐Membered and Larger Carbocycles
References
Chapter 8 Heterocycles from Cycloaddition of Alkynes
8.1 Four‐membered Heterocycles
8.2 Five‐membered Heterocycles
8.2.1 Pyrroles, Furans, and Thiophenes Synthesis
8.2.2 Indoles, Benzo[b]Furans, Benzo[b]Thiophenes, and Benzo[b]Selenophenes
8.2.3 Five‐membered Rings with Two Heteroatoms
8.3 Six‐membered Heterocycles
8.3.1 Pyridine Derivatives via Cycloaddition of Alkynes with Nitriles
8.3.2 Benzopyridine Derivatives (Quinolines and Isoquinolines)
8.3.3 2‐Pyridone Derivatives and Their Benzo‐derivatives (Quinolinones and Isoquinolonones)
8.3.4 Six‐membered N‐heterocycles Having Two Nitrogen Atoms
8.3.5 2‐Pyrone, Coumarin, Isocoumarin, and Chromone Derivatives
8.4 Other Heterocycles
References
Chapter 9 Carbonyl Compounds from Alkynes and Alkenes
9.1 Hydration of Alkynes
9.2 Hydroformylation of Alkynes and Alkenes
9.2.1 Hydroformylation of Alkynes
9.2.2 Hydroformylation of Alkenes
9.3 Hydroacylation of Alkynes and Alkenes
9.4 Hydroamidation of Alkynes and Alkenes
9.5 Hydrocarboxylation of Alkynes and Alkenes
9.6 Hydroesterification of Alkynes and Alkenes
9.7 Carbonylation of Alkynes and Alkenes
9.7.1 Carbonylation of Alkynes
9.7.2 Carbonylation of Alkenes
9.7.3 Cyclocarbonylation of Alkynes and/or Alkenes
References
Chapter 10 Natural Product Synthesis via Alkyne Transformation
10.1 Hydrofunctionalization of Alkynes in Natural Product Synthesis
10.2 Double Functionalization of Alkynes in Natural Product Synthesis
10.3 Cycloaddition of Alkynes in Natural Product Synthesis
10.4 Carbonylation of Alkynes in Natural Product Synthesis
References
Index
EULA