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Practical Synthetic Organic Chemistry


Practical Synthetic Organic Chemistry

Reactions, Principles, and Techniques
2. Aufl.

von: Stéphane Caron

116,99 €

Verlag: Wiley
Format: EPUB
Veröffentl.: 06.02.2020
ISBN/EAN: 9781119448907
Sprache: englisch
Anzahl Seiten: 848

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Beschreibungen

This book is a hands-on guide for the organic chemist. Focusing on the most reliable and useful reactions, the chapter authors provide the information necessary for a chemist to strategically plan a synthesis, as well as repeat the procedures in the laboratory.<br /><br /> <ul> <li>Consolidates all the key advances/concepts in one book, covering the most important reactions in organic chemistry, including substitutions, additions, eliminations, rearrangements, oxidations, reductions</li> <li>Highlights the most important reactions, addressing basic principles, advantages/disadvantages of the methodology, mechanism, and techniques for achieving laboratory success</li> <li>Features new content on recent advances in CH activation, photoredox and electrochemistry, continuous chemistry, and application of biocatalysis in synthesis</li> <li>Revamps chapters to include new and additional examples of chemistry that have been demonstrated at a practical scale</li> </ul>
<p>List of Contributors xxxi</p> <p>Preface xxxiii</p> <p><b>1 Aliphatic Nucleophilic Substitution </b><b>1<br /></b><i>Jade D. Nelson</i></p> <p>1.1 Introduction 1</p> <p>1.2 Oxygen Nucleophiles 1</p> <p>1.3 Phosphorus Nucleophiles 21</p> <p>1.4 Sulfur Nucleophiles 21</p> <p>1.5 Nitrogen Nucleophiles 26</p> <p>1.6 Halogen Nucleophiles 38</p> <p>1.7 Carbon Nucleophiles 47</p> <p>1.8 Nucleophilic Substitution at a Sulfonyl Sulfur Atom 60</p> <p><b>2 Addition to Carbon-Heteroatom Multiple Bonds </b><b>65<br /></b><i>Prantik Maity and Rajappa Vaidyanathan</i></p> <p>2.1 Introduction 66</p> <p>2.2 Addition of Water to Aldehydes and Ketones: Formation of Hydrates 66</p> <p>2.3 Addition of Bisulfite to Aldehydes and Ketones 67</p> <p>2.4 The Addition of Alcohols to Aldehydes and Ketones: Acetal Formation 69</p> <p>2.5 The Addition of Thiols to Aldehydes and Ketones: S,S-Acetal Formation 71</p> <p>2.6 Reductive Etherification 72</p> <p>2.7 Addition of NH<sub>3</sub>, RNH<sub>2</sub>, and R<sub>2</sub>NH 74</p> <p>2.8 Formation of Hydrazones 79</p> <p>2.9 Formation of Oximes 80</p> <p>2.10 The Formation of gem-Dihalides from Aldehydes and Ketones 80</p> <p>2.11 The Aldol Reaction 82</p> <p>2.12 Allylorganometallics: Stannane, Borane, and Silane 92</p> <p>2.13 The Nozaki&ndash;Hiyama&ndash;Kishi Reaction 97</p> <p>2.14 Addition of Transition Metal Alkynylides to Carbonyl Compounds 99</p> <p>2.15 Addition of Organometallic Reagents to Carbonyls 100</p> <p>2.17 The Reformatsky Reaction 104</p> <p>2.18 The Wittig Reaction 106</p> <p>2.19 Horner&ndash;Wadsworth&ndash;Emmons Reaction 108</p> <p>2.20 Peterson Olefination 109</p> <p>2.21 Julia&ndash;Lythgoe Olefination 110</p> <p>2.22 Tebbe Methylenation 112</p> <p>2.23 The Mannich Reaction 113</p> <p>2.24 The Strecker Reaction 115</p> <p>2.25 Hydrolysis of Carbon&ndash;Nitrogen Double Bonds 117</p> <p>2.26 Conversion of Carboxylic Acids to Acyl Chlorides 118</p> <p>2.27 Synthesis of Acyl Fluorides from Carboxylic Acids 122</p> <p>2.28 Formation of Amides from Carboxylic Acids 123</p> <p>2.29 Formation of Amides from Esters 130</p> <p>2.30 Hydrolysis of Acyl Halides 132</p> <p>2.31 Conversion of Carboxylic Acids to Esters 132</p> <p>2.32 Hydrolysis of Amides 136</p> <p>2.33 Conversion of N-Acyloxazolidinones to Other Carboxyl Derivatives 139</p> <p>2.34 Alcoholysis of Amides 140</p> <p>2.35 Hydrolysis of Esters 141</p> <p>2.36 Transesterification 143</p> <p>2.37 Alkyl Thiol Addition to Esters 144</p> <p>2.38 Addition of Organometallic Reagents to Carboxylic Acid Derivatives 145</p> <p>2.39 The Kulinkovich Cyclopropanation 149</p> <p>2.40 Synthesis of Acyl Cyanides 150</p> <p>2.41 The Ritter Reaction 151</p> <p>2.42 Thorpe Reaction 154</p> <p>2.43 Addition of Organometallic Reagents to Nitriles 155</p> <p>2.44 Conversion of Nitriles to Amides, Esters, and Carboxylic Acids 155</p> <p>2.45 Conversion of Nitriles to Thioamides 158</p> <p>2.46 The Addition of Ammonia or Amines to Nitriles 160</p> <p>2.47 The Addition of Alcohol to Nitriles 161</p> <p>2.48 Alkyl Thiol Addition to Nitriles 162</p> <p>2.49 The Blaise Reaction 162</p> <p>2.50 The Addition of Alcohols to Isocyanates 163</p> <p>2.51 The Addition of Amines and Amides to Isocyanates 164</p> <p>2.52 The Formation of Xanthates 165</p> <p>2.53 The Addition of Amines to Carbon Dioxide 166</p> <p>2.54 The Addition of Amines to Carbon Disulfide 167</p> <p>2.55 Addition of Organometallic Reagents to Carbon Dioxide 167</p> <p><b>3 Addition to Carbon&ndash;Carbon Multiple Bonds </b><b>169<br /></b><i>John A. Ragan</i></p> <p>3.1 Introduction 169</p> <p>3.2 Hydrogen&ndash;Halogen Addition (Hydrohalogenation) 169</p> <p>3.3 Hydrogen&ndash;Oxygen Addition 173</p> <p>3.4 Hydrogen&ndash;Nitrogen Addition (Hydroamination) 178</p> <p>3.5 Hydrogen&ndash;Carbon Addition (Hydroalkylation) 180</p> <p>3.6 Halogen&ndash;Halogen Addition 191</p> <p>3.7 Hydroxy&ndash;Halogen Addition 192</p> <p>3.8 Amino&ndash;Halogen Addition 194</p> <p>3.9 Carbon&ndash;Halogen Addition 194</p> <p>3.10 Oxygen&ndash;Oxygen Addition 196</p> <p>3.11 Oxygen&ndash;Nitrogen Addition 202</p> <p>3.12 Nitrogen&ndash;Nitrogen Addition 204</p> <p>3.13 Carbon&ndash;Oxygen Addition 206</p> <p>3.14 Carbon&ndash;Nitrogen Addition 211</p> <p>3.15 Carbon&ndash;Carbon Addition 212</p> <p><b>4 Nucleophilic Aromatic Substitution </b><b>231<br /></b><i>St&eacute;phane Caron and Emma McInturff</i></p> <p>4.1 Introduction 231</p> <p>4.2 Oxygen Nucleophiles 232</p> <p>4.3 Sulfur Nucleophiles 234</p> <p>4.4 Nitrogen Nucleophiles 236</p> <p>4.5 Halogen Nucleophiles 241</p> <p>4.6 Carbon Nucleophiles 243</p> <p>4.7 ortho-Arynes 245</p> <p><b>5 Electrophilic Aromatic Substitution </b><b>247</b></p> <p><i>St&eacute;phane Caron and Emma McInturff</i></p> <p>5.1 Introduction 247</p> <p>5.2 Nitrogen Electrophiles 247</p> <p>5.3 Sulfur Electrophiles 250</p> <p>5.4 Halogenation 253</p> <p>5.5 Carbon Electrophiles 257</p> <p><b>6 Selected Catalytic Reactions </b><b>269<br /></b><i>Sebastien Monfette, Adam R. Brown, Pascal Dub&eacute;, Nathan D. Ide, Chad A. Lewis, Jared L. Piper,&nbsp;</i><i>Shashank Shekhar, and Shu Yu</i></p> <p>6.1 Introduction 269</p> <p>6.2 Organoboron Reagents:The Suzuki&ndash;Miyaura Coupling 270</p> <p>6.3 Organomagnesium Reagents: Kumada&ndash;Corriu Coupling 282</p> <p>6.4 Organozinc Reagents: Negishi Coupling 287</p> <p>6.5 Cross-Electrophile Coupling 291</p> <p>6.6 Organotin Reagents: The Stille Coupling (Migita-Stille Reaction) 292</p> <p>6.7 Cross-Coupling Reactions with Organosilicon Compounds 295</p> <p>6.8 Metal-catalyzed Coupling of Alkynes (Sonogashira Coupling) 296</p> <p>6.9 Metal-Catalyzed Coupling of Alkenes (Heck Coupling) 298</p> <p>6.10 Enolate Arylations 303</p> <p>6.11 Pd- and Cu-Catalyzed Aryl C&mdash;N Bond Formation 306</p> <p>6.12 Pd- and Cu-Catalyzed Aryl C&mdash;O Bond Formation 320</p> <p>6.13 Pd- and Cu-Catalyzed Aryl C&mdash;S Bond Formation 322</p> <p>6.14 Aryl C&mdash;B Bond Formation 324</p> <p>6.15 Pd-Catalyzed Aryl C&mdash;CN Bond Formation 327</p> <p>6.16 Metal-Catalyzed Allylic Substitution 329</p> <p>6.17 Catalytic Metal-Mediated Methods for Fluorination 337</p> <p>6.18 Selected Metal-Mediated C&mdash;H Functionalization 347</p> <p>6.19 C&mdash;X Bond Forming Reactions via Borrowed Hydrogen Methodologies 357</p> <p>6.20 Alkene and Alkyne Metathesis Reactions 362</p> <p>6.21 Organocatalysis 369</p> <p><b>7 Rearrangements </b><b>377<br /></b><i>David H. Brown Ripin and Chad A. Lewis</i></p> <p>7.1 Introduction 377</p> <p>7.2 [1,2]-Rearrangements 377</p> <p>Other Rearrangements 402</p> <p>7.3 Other Rearrangements 402</p> <p>7.4 Miscellaneous Migrations 420</p> <p><b>8 Eliminations </b><b>425<br /></b><i>Sally Gut Ruggeri</i></p> <p>8.1 Introduction 425</p> <p>8.2 Formation of Alkenes 425</p> <p>8.3 Formation of Dienes 438</p> <p>8.4 Formation of Alkynes 442</p> <p>8.5 Formation of C=N bonds 444</p> <p>8.6 Formation of Nitriles 445</p> <p>8.7 Formation of Ketenes and Related Compounds 447</p> <p>8.8 Fragmentations 449</p> <p>8.9 Dehydrating Reagents 451</p> <p><b>9 Reductions </b><b>455<br /></b><i>Sally Gut Ruggeri, St&eacute;phane Caron, Pascal Dub&eacute;, Nathan D. Ide, Kristin E. Price Wiglesworth, John A. Ragan, and Shu Yu</i></p> <p>9.1 Introduction 455</p> <p>9.2 Reduction of C&mdash;C Bonds 455</p> <p>9.3 Reduction of C&mdash;N Bonds 471</p> <p>9.4 Reduction of C&mdash;O Bonds 479</p> <p>9.5 Reduction of C&mdash;S Bonds 494</p> <p>9.6 Reduction of C&mdash;X Bonds 500</p> <p>9.7 Reduction of Heteroatom&ndash;Heteroatom Bonds 504</p> <p><b>10 Oxidations </b><b>513<br /></b><i>Eric C. Hansen, Robert Perkins, and David H. Brown Ripin</i></p> <p>10.1 Introduction 513</p> <p>10.2 Oxidation of C&mdash;C Single and Double Bonds 514</p> <p>10.3 Oxidation of C&mdash;H Bonds 520</p> <p>10.4 Oxidation of Carbon&ndash;Oxygen Bonds and at Carbon Bearing an Oxygen Substituent 536</p> <p>10.5 Oxidation of Aldehydes to Carboxylic Acids and Derivatives 543</p> <p>10.6 Oxidation of Carbon&ndash;Nitrogen Bonds and at Carbon Bearing a Nitrogen Substituent 546</p> <p>10.7 Oxidation of Nitrogen Functionalities 548</p> <p>10.8 Oxidation of Sulfur and at Carbon Adjacent to Sulfur 555</p> <p>10.9 Oxidation of Other Functionality 561</p> <p><b>11 Selected Free Radical Reactions </b><b>563<br /></b><i>Christophe Allais, Eric C. Hansen, Nathan D. Ide, Robert J. Perkins, and Elizabeth C. Swift</i></p> <p>11.1 Introduction 563</p> <p>11.2 Radical Reactions via Chemical Initiation 563</p> <p>11.3 Photoredox Catalysis 575</p> <p>11.4 Electrochemical Methods 583</p> <p><b>12 Synthesis of &ldquo;Nucleophilic&rdquo; Organometallic Reagents </b><b>591<br /></b><i>David H. Brown Ripin and Adam R. Brown</i></p> <p>12.1 Introduction 591</p> <p>12.2 Synthesis of &ldquo;Nucleophilic&rdquo; Organometallic Reagents 592</p> <p>12.3 Strategies for Metalating Heterocycles 615</p> <p>12.4 Reactions of &ldquo;Nucleophilic&rdquo; Organometallic Reagents 618</p> <p><b>13 Synthesis of Common Aromatic Heterocycles </b><b>621<br /></b><i>St&eacute;phane Caron</i></p> <p>13.1 Introduction 621</p> <p>13.2 Pyrroles 623</p> <p>13.3 Indoles 624</p> <p>13.4 2-Indolinones (Oxindoles) 626</p> <p>13.5 Isatins (2,3-Indolindiones) 628</p> <p>13.6 Carbazoles 628</p> <p>13.7 Pyrazoles 629</p> <p>13.8 Indazoles 630</p> <p>13.9 Imidazoles and Benzimidazoles 631</p> <p>13.10 1,2,3-Triazoles and Benzotriazole 633</p> <p>13.11 1,2,4-Triazoles 635</p> <p>13.12 Tetrazoles 635</p> <p>13.13 Dihydropyridines 637</p> <p>13.14 Pyridines 637</p> <p>13.15 Quinolines 639</p> <p>13.16 Quinolinones and 2-Hydroxyquinolines 641</p> <p>13.17 Isoquinolines 642</p> <p>13.18 Isoquinolinones 643</p> <p>13.19 Quinolones (4-Hydroxyquinolines) 644</p> <p>13.20 Pyrimidines and Pyrimidones 645</p> <p>13.21 Quinazolines and Quinazolinones 647</p> <p>13.22 Pyrazines and Quinoxalines 648</p> <p>13.23 Pyridazines, Phtalazines, and Cinnolines 650</p> <p>13.24 1,2,4-Triazines 651</p> <p>13.25 Furans and Benzofurans 652</p> <p>13.26 Benzopyran-4-One (Chromen-4-One, Flavone) and Xanthone 653</p> <p>13.27 Coumarins 655</p> <p>13.28 Thiophenes and Benzothiophenes 656</p> <p>13.29 Isoxazoles and Benzisoxazoles 657</p> <p>13.30 Oxazoles and Benzoxazoles 659</p> <p>13.31 Isothiazoles and Benzisothiazoles 660</p> <p>13.32 Thiazoles and Benzothiazoles 661</p> <p>13.33 1,2,4-Oxadiazoles 662</p> <p>13.34 1,3,4-Oxadiazoles 663</p> <p><b>14 Access to Chirality </b><b>665<br /></b><i>Angela L. A. Puchlopek-Dermenci and Robert W. Dugger</i></p> <p>14.1 Introduction 665</p> <p>14.2 Using the Chiral Pool 665</p> <p>14.3 Classical Resolutions 668</p> <p>14.4 Dynamic Kinetic Resolutions 673</p> <p>14.5 Desymmetrization of Meso Compounds 675</p> <p>14.6 Chiral Chromatography 676</p> <p><b>15 Biocatalysis </b><b>679<br /></b><i>Carlos A. Martinez, Rajesh Kumar, and John Wong</i></p> <p>15.1 Introduction 679</p> <p>15.2 Group Transfer Reactions 682</p> <p>15.3 Reductions 688</p> <p>15.4 Oxidations 693</p> <p>15.5 C&mdash;C Bond Forming Reactions 699</p> <p>15.6 Future Developments 703</p> <p><b>16 Green Chemistry </b><b>705<br /></b><i>Juan Colberg, Jared L. Piper, and John Wong</i></p> <p>16.1 Introduction 705</p> <p>16.2 Green Chemistry Metrics 706</p> <p>16.3 Solvent and Reagent Selection 710</p> <p>16.4 Green Reactions/Reagents 716</p> <p>16.5 Examples of Green Methods and Reagents for Common Reaction Types 716</p> <p>16.6 Predictive Tools to Design for Green Chemistry 724</p> <p>16.7 Green Chemistry Improvements in Process Development 725</p> <p><b>17 Continuous Chemistry </b><b>729<br /></b><i>David D. Ford, Robert J.Maguire, J. Christopher McWilliams, Bryan Li, and Jared L. Piper</i></p> <p>17.1 Introduction 729</p> <p>17.2 Aliphatic Nucleophilic Substitutions 731</p> <p>17.3 Additions to C&mdash;Het Multiple Bonds 735</p> <p>17.4 Addition to C&mdash;C Multiple Bonds 735</p> <p>17.5 Nucleophilic Aromatic Substitutions 739</p> <p>17.6 Electrophilic Aromatic Substitution 739</p> <p>17.7 Catalysis 741</p> <p>17.8 Rearrangements 743</p> <p>17.9 Eliminations 746</p> <p>17.10 Reductions 748</p> <p>17.11 Oxidations 751</p> <p>17.12 Free Radical Reactions 757</p> <p>17.13 Syntheses of Organometallic Reagents 760</p> <p>17.14 Synthesis of Aromatic Heterocycles 766</p> <p>17.15 Access to Chirality 770</p> <p>17.16 Biotransformations 771</p> <p><b>18 General Solvent Properties </b><b>773<br /></b><i>St&eacute;phane Caron</i></p> <p>18.1 Introduction 773</p> <p>18.2 Definitions and Acronyms 774</p> <p>18.3 Solvent Properties 775</p> <p>18.4 Mutual Solubility of Water and Organic Solvents 778</p> <p>18.5 Other Useful Information on Solvents 779</p> <p>18.6 Solvent Safety 780</p> <p>18.7 Risk Phrases Used in the Countries of EU 781</p> <p><b>19 Practical Chemistry Concepts Tips for the Practicing Chemist or Things They Don&rsquo;t Teach You in School </b><b>785<br /></b><i>Sally Gut Ruggeri</i></p> <p>19.1 Introduction 785</p> <p>19.2 Reaction Execution 785</p> <p>19.3 Solvents and Reagents 788</p> <p>19.4 Isolation 793</p> <p>19.5 Analysis 797</p> <p>Subject Index 801</p> <p>Combo Index 811</p>
<p><b>Stéphane Caron</b> is an Executive Director in Chemical Research & Development at Pfizer Inc.
<p><b>Presents the principles, techniques, and reactions of practical synthetic organic chemistry</b> <p><i>Practical Synthetic Organic Chemistry: Reactions, Principles, and Techniques, Second Edition</i> is a valuable desktop reference for professionals working in and students studying organic chemistry or related fields. <p>Building on the framework of the first edition, it exemplifies the majority of useful reactions and highlights the most reliable experimental conditions selected by industrial process chemists from pharmaceutical companies. It provides the information necessary for a chemist to strategically plan a synthesis, rapidly select reagents and procedures to maximize success in the laboratory. <p>In <i>Practical Synthetic Organic Chemistry: Reactions, Principles, and Techniques, Second Edition,</i> reaction chapters offer information on the basics of the reaction, the synthetic procedure(s), and scope of the reaction. Later chapters discuss practical solvents and green chemistry concepts. It also guides the reader to a wealth of useful references from the primary literature. <ul> <li>Consolidates all the key advances/concepts in one book, covering the most important reactions in organic chemistry, including substitutions, additions, eliminations, rearrangements, oxidations, and reductions</li> <li>Features new content on recent advances in CH activation, photoredox and electrochemistry, continuous chemistry, and the application of biocatalysis in synthesis</li> <li>Updates chapters to include new and additional examples of chemistry that have been demonstrated at a practical scale</li> </ul> <p>This book highlights the most important reactions, addressing basic principles, advantages/ disadvantages of the methodology, mechanism, and techniques for achieving laboratory success.

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