Visible light photocatalysis in organic chemistry /
edited by Corey R.J. Stephenson, Tehshik P. Yoon, and David W.C. MacMillan.
- 1 online resource
Includes bibliographical references and index.
Cover; Title Page; Copyright; Contents; Chapter 1 An Overview of the Physical and Photophysical Properties of [Ru(bpy)3]2+; 1.1 Introduction; 1.2 [Ru(bpy)3]2+: Optical and Electrochemical Properties; 1.2.1 Optical Properties; 1.2.2 Electrochemical Properties; 1.3 Excited State Kinetics; 1.3.1 Steady-State Emission; 1.3.2 Time-Resolved Emission; 1.4 Excited-State Reactivity of [Ru(bpy)3]2+; 1.5 Energy Transfer: FÃœrster and Dexter Mechanisms; 1.6 Electron Transfer; 1.7 Probing the Mechanism, Stage I: Sternâ#x80;#x93;Volmer Quenching Studies. 1.8 Probing the Mechanism, Stage II: Electron Versus Energy Transfer1.9 Designing Photocatalysts: [Ru(bpy)3]2+ as a Starting Point; 1.10 Conclusion; References; Chapter 2 Visible-Light-Mediated Free Radical Synthesis; 2.1 Introduction; 2.2 Basics of the Photocatalytic Cycle; 2.3 Generation of Radicals; 2.3.1 Formation of C-Centered Radicals; 2.3.1.1 Dehalogenation (I, Br, Cl); 2.3.1.2 Other C-Heteroatom Cleavage; 2.3.1.3 C-C Bond Cleavage; 2.3.2 Formation of N-Centered Radicals; 2.4 C-X Bond Formation; 2.4.1 C-O Bond; 2.4.2 C-N Bond; 2.4.3 C-S and C-Se Bonds; 2.4.4 C-Br Bond; 2.4.5 C-F Bond. 2.4.6 C-B Bond2.5 C-C Bond Formation; 2.5.1 Formation and Reactivity of Aryl Radicals; 2.5.2 Formation and Reactivity of Trifluoromethyl and Related Radicals; 2.5.2.1 Photocatalyzed Reduction of Perfluorohalogen Derivatives; 2.5.2.2 Photocatalyzed Reduction of Perfluoroalkyl-Substituted Onium Salts; 2.5.2.3 Photocatalyzed Formation of Perfluoroalkyl Radicals from Sulfonyl and Sulfinyl Derivatives; 2.5.3 Formation and Reactivity of Alkyl and Related Radicals; 2.5.3.1 C-C Bond Formation Through Photocatalyzed Reduction of Halogen Derivatives and Analogs. 2.5.3.2 C-C Bond Formation Through Photocatalyzed Oxidation of Electron-Rich Functional Group2.5.3.3 C-C Bond Formation Through Photocatalyzed Oxidation of Amino Group; 2.6 Radical Cascade Applications; 2.6.1 Intramolecular Polycyclization Processes; 2.6.2 Sequential Inter- and Intramolecular Processes; 2.6.3 Sequential Radical and Polar Processes; References; Chapter 3 Atom Transfer Radical Addition using Photoredox Catalysis; 3.1 Introduction; 3.2 Transition Metal-Catalyzed ATRA; 3.2.1 Ruthenium- and Iridium-Based ATRA; 3.2.1.1 Mechanistic Investigations. 3.2.1.2 Ruthenium- and Iridium-Based ATRA3.2.2 Copper-Mediated ATRA; 3.2.2.1 Trifluoromethylation; 3.3 Other Photocatalysts for ATRA Transformations; 3.3.1 p-Anisaldehyde; 3.4 Semiconductor; 3.5 Atom Transfer Radical Cyclization (ATRC); 3.6 Atom Transfer Radical Polymerization (ATRP); 3.7 Conclusion; References; Chapter 4 Visible Light Mediated -Amino C-H Functionalization Reactions; 4.1 Introduction; 4.2 Visible Light Mediated -Amino C-H Functionalization Via Iminium Ions; 4.2.1 Aza-Henry Reaction; 4.2.2 Mannich Reaction; 4.2.3 Strecker Reaction; 4.2.4 Friedelâ#x80;#x93;Crafts Reaction.
Filling the need for a ready reference that reflects the vast developments in this field, this book presents everything from fundamentals, applications, various reaction types, and technical applications. Edited by rising stars in the scientific community, the text focuses solely on visible light photocatalysis in the context of organic chemistry. This primarily entails photo-induced electron transfer and energy transfer chemistry sensitized by polypyridyl complexes, yet also includes the use of organic dyes and heterogeneous catalysts. A valuable resource to the synthetic organic community, polymer and medicinal chemists, as well as industry professionals.