Practical Functional Group Synthesis E-Book

Robert A. Stockland

• Herausgeber: John Wiley & Sons
• Kategorie: Wissenschaft und neue Technologien
• Sprache: Englisch

Seitenzahl: 1110

Veröffentlichungsjahr: 2016

Beschreibung

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

Leseprobe

Table of Contents

COVER

TITLE PAGE

PREFACE

ACKNOWLEDGMENTS

1 INTRODUCTION TO PRACTICAL FUNCTIONAL GROUP SYNTHESIS

1.1 GENERAL APPROACHES FOR DESIGNING SYNTHESES

1.2 NEW VERSIONS OF “CLASSIC” ORGANIC REACTIONS

1.3 SOLVENT SELECTION AND SOLVENT-FREE REACTIONS

1.4 OPERATIONAL SIMPLICITY

1.5 METAL-CATALYZED TRANSFORMATIONS

1.6 ORGANOCATALYSIS

1.7 MICROWAVE- AND ULTRASOUND-ASSISTED CHEMISTRY

1.8 SUSTAINABILITY

1.9 ASYMMETRIC SYNTHESIS

REFERENCES

2 PREPARATION OF ALCOHOLS, ETHERS, AND RELATED COMPOUNDS

2.1 PREPARATION OF ALCOHOLS, ETHERS, AND RELATED COMPOUNDS THROUGH THE FORMATION OF OXYGEN–CARBON(

SP

3

) BONDS

2.2 PREPARATION OF PHENOLS, ARYL ETHERS, AND RELATED COMPOUNDS THROUGH THE FORMATION OF OXYGEN–CARBON(

SP

2

) BONDS

2.3 PREPARATION OF VINYL ETHERS AND RELATED COMPOUNDS THROUGH THE FORMATION OF OXYGEN–CARBON(

SP

2

) BONDS

2.4 PREPARATION OF ALKYNYL ETHERS AND RELATED COMPOUNDS THROUGH THE FORMATION OF OXYGEN–CARBON(

SP

) BONDS

REFERENCES

3 SYNTHESIS OF AMINES, AMIDES, AND RELATED COMPOUNDS

ALKYLAMINES

3.1 SYNTHESIS OF ALKYLAMINES AND RELATED COMPOUNDS THROUGH NITROGEN–CARBON(

SP

3

) BOND-FORMING REACTIONS

3.2 SYNTHESIS OF ARYLAMINES AND RELATED COMPOUNDS THROUGH NITROGEN–CARBON(

SP

2

) BOND-FORMING REACTIONS

3.3 SYNTHESIS OF VINYLAMINES AND RELATED COMPOUNDS THROUGH NITROGEN–CARBON(

SP

2

) BOND-FORMING REACTIONS

3.4 SYNTHESIS OF YNAMIDES AND RELATED COMPOUNDS THROUGH NITROGEN–CARBON(

SP

) BOND-FORMING REACTIONS

REFERENCES

4 SYNTHESIS OF ORGANOPHOSPHINES, PHOSPHONATES, AND RELATED COMPOUNDS

4.1 INTRODUCTION TO THE SYNTHESIS OF ORGANOPHOSPHORUS COMPOUNDS GENERATED THROUGH THE FORMATION OF PHOSPHORUS–CARBON BONDS

4.2 SYNTHESIS OF ALKYLPHOSPHINES AND RELATED COMPOUNDS THROUGH THE FORMATION OF PHOSPHORUS–CARBON(

SP

3

) BONDS

4.3 SYNTHESIS OF ARYLPHOSPHINES AND RELATED COMPOUNDS THROUGH THE FORMATION OF PHOSPHORUS–CARBON(

SP

2

) BONDS

4.4 SYNTHESIS OF VINYLPHOSPHINES AND RELATED COMPOUNDS THROUGH THE FORMATION OF PHOSPHORUS–CARBON(

SP

2

) BONDS

4.5 SYNTHESIS OF ALKYNYLPHOSPHINES AND RELATED COMPOUNDS THROUGH THE FORMATION OF PHOSPHORUS–CARBON(

SP

) BONDS

REFERENCES

5 SYNTHESIS OF THIOETHERS, SULFONES, AND RELATED COMPOUNDS

5.1 SYNTHESIS OF THIOETHERS AND RELATED COMPOUNDS THROUGH THE FORMATION OF SULFUR–CARBON(

SP

3

) BONDS

5.2 SYNTHESIS OF ARYL THIOETHERS AND RELATED COMPOUNDS THROUGH THE FORMATION OF SULFUR–CARBON(

SP

2

) BONDS

5.3 SYNTHESIS OF VINYL THIOETHERS AND RELATED COMPOUNDS THROUGH THE FORMATION OF SULFUR–CARBON(

SP

2

) BONDS

5.4 SYNTHESIS OF THIOETHERS AND RELATED COMPOUNDS THROUGH THE FORMATION OF SULFUR–CARBON(

SP

) BONDS

REFERENCES

6 SYNTHESIS OF ORGANOBORONIC ACIDS, ORGANOBORONATES, AND RELATED COMPOUNDS

6.1 SYNTHESIS OF ALKYLBORONATES AND RELATED COMPOUNDS THROUGH THE FORMATION OF BORON–CARBON(SP

3

) BONDS

6.2 SYNTHESIS OF ARYLBORONATES AND RELATED COMPOUNDS THROUGH THE FORMATION OF BORON–CARBON(SP

2

) BONDS

6.3 SYNTHESIS OF VINYLBORONATES AND RELATED COMPOUNDS THROUGH THE FORMATION OF BORON–CARBON(

SP

2

) BONDS

6.4 SYNTHESIS OF ALKYNYLBORONATES AND RELATED COMPOUNDS THROUGH THE FORMATION OF BORON–CARBON(

SP

) BONDS

REFERENCES

7 SYNTHESIS OF ORGANOHALIDES

7.1 SYNTHESIS OF ALKYL HALIDES THROUGH THE FORMATION OF HALOGEN–CARBON(

SP

3

) BONDS

7.2 SYNTHESIS OF ARYL HALIDES THROUGH THE FORMATION OF HALOGEN–CARBON(

SP

2

) BONDS

7.3 SYNTHESIS OF VINYL HALIDES THROUGH THE FORMATION OF HALOGEN–CARBON(

SP

2

) BONDS

7.4 SYNTHESIS OF ALKYNYL HALIDES THROUGH THE FORMATION OF HALOGEN–CARBON(

SP

) BONDS

REFERENCES

INDEX

END USER LICENSE AGREEMENT

List of Tables

Chapter 01

Table 1.1 Effect of Microwave Power on the Product Distribution of a

Phospha

-Michael Addition [52].

List of Illustrations

Chapter 01

SCHEME 1.1 Synthesis of alkyl aryl ethers using the cuprous iodide/phen catalyst system [5].

SCHEME 1.2 Synthesis of diaryl ethers using a discrete copper complex [6].

SCHEME 1.3 Synthesis of alkyl aryl ethers using aryltrifluoroborate salts [7].

SCHEME 1.4 Effect of solvent on the double hydrophosphination of alkynes [9].

FIGURE 1.1 Solvent-free reaction using both a solid and a liquid reagent.

FIGURE 1.2 Stability of common trialkylphosphines and dialkylbiarylphosphines.

SCHEME 1.5 Example of a rhodium-catalyzed carbon–oxygen bond-forming reaction [17].

SCHEME 1.6 Example of an asymmetric palladium-catalyzed carbon–nitrogen bond-forming reaction [18].

SCHEME 1.7 Example of a palladium-catalyzed carbon–phosphorus bond-forming reaction [19].

SCHEME 1.8 Example of a decarboxylative copper-promoted carbon–phosphorus bond-forming reaction [20].

SCHEME 1.9 Examples of a palladium-catalyzed carbon–fluorine bond-forming reaction [21].

SCHEME 1.10 Organocatalytic asymmetric synthesis of functionalized tetrahydrothiophenes [35].

SCHEME 1.11 Organocatalytic asymmetric synthesis of chromane derivatives [36].

SCHEME 1.12 Microwave-assisted aqueous alkylation of amines using an open vessel [47].

FIGURE 1.3 General relationship between the polarity of the solvent and the ability of the solvent to absorb microwave energy.