Side Reactions in Organic Synthesis II Aromatic Substitutions

This new textbook is the successor to the volume "Side Reactions in Organic Synthesis - A Guide to Successful Synthesis Design" (2004), written by the same author. Whereas the predecessor mainly covered the limitations of aliphatic substitution reactions, this new volume focuses on the most important aromatic substitution reactions, both electrophilic and nucleophilic, such as amination reactions, halogenation reactions, Friedel-Crafts acylations, or transition metal-catalyzed arylation reactions. Each chapter not only describes the scope of a specific reaction type, but also reveals what cannot be achieved with this reaction, i.e. what type of side reactions are to be expected with certain starting materials or electrophiles/nucleophiles. With its unique approach, this is a must-have book for graduate students in organic chemistry and synthetic chemists both in academia and industry!

Preface

ELECTROPHILIC ALKYLATION OF ARENES
General Aspects
Problematic Arenes
Problematic Electrophiles

ELECTROPHILIC OLEFINATION OF ARENES
General Aspects
Olefinations with Leaving-Group-Substituted Olefins
Olefinations with Unsubstituted Olefins
Olefinations with Alkynes

ELECTROPHILIC ARYLATION OF ARENES
General Aspects
Arylations with Aryl Halides
Arylations with Diazonium Salts
Arylations with Other Functionalized Arenes
Arylations with Unsubstituted Arenes

ELECTROPHILIC ACYLATION OF ARENES
General Aspects
Problematic Arenes
Problematic Electrophiles

ELECTROPHILIC HALOGENATION OF ARENES
General Aspects
Typical Side Reactions
Regioselectivity
Catalysis
Fluorinations
Electron-Deficient Arenes
Electron-Rich Arenes
Sensitive Functional Groups

ELECTROPHILIC FORMATION OF AROMATIC C-N BONDS
Nitration of Arenes
Electrophilic Aromatic Aminations
Electrophilic Aromatic Amidations

ELECTROPHILIC FORMATION OF AROMATIC C-S BONDS
Sulfonylation
Sulfinylation
Sulfenylation

AROMATIC NUCLEOPHILIC SUBSTITUTIONS
General Aspects
Problematic Electrophiles
Problematic Nucleophiles

EPILOGUE: ECONOMICS, POLITICS, AND THE QUALITY OF CHEMICAL RESEARCH
Prosperity
Slavery and Freedom
The Quality of Chemical Research

Index

Florencio Zaragoza Dorwald studied chemistry at the Georg-August University in Gottingen, Germany, and Universite Louis Pasteur, Strasbourg, France, where he obtained his Ph.D. in 1990 on the synthesis of natural products under the guidance of M. Franck-Neumann and M. Miesch. He spent one postdoctoral year in both the groups of A. Pfaltz (University of Basel) and A. P. Marchand (University of North Texas), and then worked on the synthesis of unnatural amino acids at the Technical University of Dresden. From 1994 to 2007 he had a position as a medicinal chemist at Novo Nordisk A/S, Denmark. Currently, he is employed as organic chemist at Lonza AG in Visp, Switzerland.