The first book of its kind to highlight iodine as a sustainable alternative to conventional transition metal catalysis

Iodine Catalysis in Organic Synthesis provides detailed coverage of recent advances in iodine chemistry and catalysis, focusing on the utilization of various iodine-containing compounds as oxidative catalysts. Featuring contributions by an international panel of leading research chemists, this authoritative volume explores the development of environmentally benign organic reactions and summarizes catalytic transformations of molecular iodine and iodine compounds such as hypervalent organoiodine and inorganic iodine salts.

Readers are first introduced to the history of iodine chemistry, the conceptual background of homogeneous catalysis, and the benefits of iodine catalysis in comparison with transition metals. Next, chapters organized by reaction type examine enantioselective transformations, catalytic reactions involving iodine, catalyst states, oxidation in iodine and iodine catalyses, and catalytic reactions based on halogen bonding. Practical case studies and real-world examples of different applications in organic synthesis and industry are incorporated throughout the text. An invaluable guide for synthetic chemists in both academic and industrial laboratories,Iodine Catalysis in Organic Synthesis:Provides a thorough overview of typical iodine-catalyzed reactions, catalyst systems, structures, and reactivityExplores promising industrial applications of iodine-based reagents for organic synthesisHighlights the advantages iodine catalysis has over classical metal-catalyzed reactionsDiscusses sustainable and eco-friendly methods in hypervalent iodine chemistry

Edited by two world authorities on the catalytic applications of organoiodine compounds,Iodine Catalysis in Organic Synthesis is required reading for catalytic, organic, and organometallic chemists, medicinal and pharmaceutical chemists, industrial chemists, and academic researchers and advanced students in relevant fields.

Kazuaki Ishihara is Full Professor, Nagoya University, Japan. He serves on the editorial advisory boards of European Journal of Organic Chemistry, Asian Journal of Organic Chemistry,and Topics in Current Chemistry.He is the author of Acid Catalysis in Modern Organic Synthesisand has published more than 350 articles in international journals.

Kilian Muñiz was ICREA Research Professor and Group Leader, Institute of Chemical Research of Catalonia (ICIQ), Tarragona, Spain. He was Vice-President of the Organic Section of the Royal Spanish Society of Chemistry and served on the advisory boards of Advanced Synthesis and Catalysis, The Chemical Record, and ACS Journal of Organic Chemistry.Professor Kilian Muñiz passed away unexpectedly in March 2020.

Preface xi

1 Historical Introduction 1
Viktor V. Zhdankin

2 Concepts in Iodine Catalysis 11
Kazuaki Ishihara

3 Catalysis by Halogen Bonding Based on Iodine 27
Revannath L. Sutar and Stefan M. Huber

4 Catalytic Transformations with R4NI Catalyst Precursors 69
Xiao-Xian Li and Yun-Fei Du

5 Catalytic Transformations Based on Iodine(I) Involving Radical Pathways 121
Alexandra E. Bosnidou and R. Martin Romero

6 Aromatic CH Functionalization 151
Mahesh Puthanveedu and Andrey P. Antonchick

7 Design of Chiral Organoiodine(I/III) Catalysts for Asymmetric Oxidative Transformations 185
Andreas Boelke and Boris J. Nachtsheim

8 Catalytic and Asymmetric Dearomatization Reactions Employing Hypervalent Iodine Reagents 211
Toshifumi Dohi and Yasuyuki Kita

9 Catalytic Alkene Difunctionalization Reactions 243
John M. Ovian and Eric N. Jacobsen

10 Catalytic Oxidative𝛂-Functionalization of Carbonyls 275
Muhammet Uyanik

11 Oxidations with Iodine(V) Compounds From Stoichiometric Compounds to Catalysts 299
Frederic Ballaschk and Stefan F. Kirsch

12 Sustainable Methods in Hypervalent Iodine Chemistry 335
Brandon Frey, Asim Maity, Hao Tan, Pritam Roychowdhury, and David C. Powers

13 Industrial Application of Iodine Catalysis 387
Tatsuo Kaiho

References 412

Index 415