Practical Functional Group Synthesis

Practical Functional Group Synthesis

Language: English

Pages: 704

ISBN: 1118612809

Format: PDF / Kindle (mobi) / ePub

Practical Functional Group Synthesis

Language: English

Pages: 704

ISBN: 1118612809

Format: PDF / Kindle (mobi) / ePub


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

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that use entirely organic compounds as catalysts [24–34]. Practical advantages of an organocatalyst can include an increased tolerance of the ­catalyst and catalytic reactions to moisture and air, greater selectivity, and the minimization MICROWAVE‐ AND ULTRASOUND‐ASSISTED CHEMISTRY  17 O C N catalyst (10%) toluene, rt, 50 h O HS O N C OtBu OtBu S (1.3 equiv) O CF3 S NH N H N H CF3 94% (99% ee; 9:1 dr) >10 related examples up to 98% up to 12:1 dr up to 99% ee catalyst

selectivities, analogous reactions carried out with more electron‐donating PREPARATION OF VINYL ETHERS AND RELATED COMPOUNDS  93 OH catalyst (5%) C6D5NO2, 120 °C, 7 h iPr iPr N O >95% 3 related examples up to >95% Cu Me N i Pr i Pr catalyst Scheme 2.84  Copper‐catalyzed intramolecular cyclization of alkynyl alcohols [124]. O Me N O N HO Me (C6F5)3PAuCl (10%) AgOTf (10%) CH2Cl2, rt, 28 h HO O A + O HO HO N Me O B 49% (A:B = >20:1) >7 related examples up to 84% up to A:B

pages cm   Includes bibliographical references and index.   ISBN 978-1-118-61280-4 (pbk.) 1.  Chemical bonds.  2.  Functional groups.  3.  Chemistry, Organic.  I.  Title.   QD461.S85 2016  547′.2–dc23 2015024767 Set in 10/12pt Times by SPi Global, Pondicherry, India Printed in the United States of America 10 9 8 7 6 5 4 3 2 1 1 2016 Contents Prefaceix Acknowledgmentsxi 1  Introduction to Practical Functional Group Synthesis 1 1.1 General Approaches for Designing Syntheses,  1 1.2

Aminofluorination is a valuable approach to the simultaneous incorporation of multiple functional groups. Using this approach, a variety of styrene derivatives were functionalized (Scheme  3.35) [33]. While a number of copper compounds promoted the reaction, the combination of a simple copper salt along with a bathocuproine ligand was the most effective. The reaction was highly regioselective and added to the fluorine to the α‐position. The metal‐free asymmetric amination of benzofuranones has

(5%) ligand (10%) additive (5%) THF, 25 °C NH2 + H N (1 equiv) 94% (92:8 er) O O Me O P P N O Me O O OH O ligand additive Caution! THF, hexane, and ethyl acetate are highly flammable. Under an argon atmosphere, an oven‐dried Schlenk tube (10 mL) was charged with 2‐cyclopenten‐1‐ol (1 mmol), aniline (0.25 mmol), followed by freshly prepared Pd(dba)2 (5 mol%), chiral phosphoric acid (5 mol%), and then the phosphoramidite ligand (10 mol%). Freshly distilled THF (1 mL) and a magnetic

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