Chemical Photocatalysis By Burkhard König (informative)
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Burkhard König
Table of Contents in Chemical Photocatalysis By Burkhard König
List of contributing authors
1 Introduction
2 Early pioneers of organic photochemistry
2.1 References
3 Photophysics of Photocatalysts
3.1 Setting the Frame
3.2 The Experimentalist’s Perspective
3.3 The Theoreticians’ Perspective: A Closer Look
3.3.1 Transition probabilities
3.3.2 Orbitals
3.4 References
4 Flavin photocatalysis
4.1 Introduction
4.1.1 General properties
4.2 Early examples of flavin photocatalysis
4.3 Flavin photocatalysis in synthesis application
4.4 Flavin-related compounds in photocatalysis
4.5 Photooxidations via singlet oxygen mechanism
4.6 Conclusion
4.7 References
5 Templated Enantioselective Photocatalysis
5.1 Introduction
5.2 Early studies. Paternò–Büchi cycloadditions of a chiral aromatic
aldehyde and cyclic enamines
5.3 Enantioselective Norrish–Yang cyclization reaction of prochiral
imidazolidinones
5.4 Enantioselective photochemical [4+4]-cycloadditions and electrocyclic
[4π]-ring closure of 2-pyridones
5.5 Enantioselective [6π]-photocyclization of acrylanilides
5.6 Enantioselective Diels–Alder reaction of a photochemically generated
ortho-quinodimethane
5.7 Formal [3+2]-photocycloadditions of 2-substituted
naphthoquinones
5.8 Intramolecular [2+2]-photocycloadditions of substituted 5,6-dihydro-
1H-pyridin-2-ones
5.9 Enantioselective radical cyclizations
5.9.1 Reductive radical cyclization reactions of 3-(ω-iodoalkylidene)-
piperidin-2-ones
5.9.2 Reductive radical cyclization of 3-(3-iodopropoxy)propenoic acid
derivatives
5.9.3 Radical cyclization reactions of 4-substituted quinolones
5.10 [2+2]-Photocycloaddition reactions of substituted
isoquinolones
5.11 [2+2]-Photocycloaddition reactions of substituted quinolones
5.11.1 Intermolecular [2+2]-photocycloaddition reactions of
quinolones
5.11.2 Intramolecular [2+2]-photocycloadditions of
4-(2′-aminoethyl)quinolones
5.11.3 Intramolecular [2+2]-photocycloadditions of 4-(ω-alkenyloxy)-quinol-
2-ones
5.12 Light-induced enantioselective catalysis
5.12.1 Photoinduced electron transfer enantioselective catalytic
reactions
5.12.2 Catalyzed enantioselective [2+2]-photocycloadditions of 4-substituted
quinolones
5.13 Conclusion
5.14 References
6 Photocatalysis with nucleic acids and peptides
6.1 Introduction
6.2 DNA-assisted enantioselective reactions
6.2.1 Photocatalytically active DNA (PhotoDNAzymes)
6.2.2 Benzophenone as photosensitizer in DNA for the development of
PhotoDNAzymes
6.3 Small peptides as organocatalysts
6.3.1 Development of peptides for photocatalytic addition to olefins
6.4 Conclusion
6.5 References
7 Visible light photoredox catalysis with [Ru(bpy)3]
2+: General principles and
the twentieth century roots
7.1 Introduction
7.2 [Ru(bpy)3]
2+ and its photoredox properties
7.3 Application of [Ru(bpy)3]
2+ as catalyst in the twentieth century
7.4 Conclusion
7.5 Abbreviations
7.6 References
8 Homogeneous visible light-mediated transition metal photoredox catalysis
other than ruthenium and iridium
8.1 Introduction
8.2 Copper in visible light catalysis
8.3 Rhenium and platinum in visible light catalysis
8.4 Iron in visible light catalysis
8.4.1 Photocatalytic oxidation of hydrocarbons
8.4.2 Photocatalytic oxidative decarboxylation
8.4.3 Oxidative degradation
8.4.4 Isomerization
8.5 Conclusion
8.6 References
9 Synergistic Visible Light Photoredox Catalysis
9.1 Introduction
9.2 Stabilized iminium ions
9.2.1 Secondary amine-catalyzed Mannich reactions
9.2.2 Coinage metal-catalyzed alkynylation reactions
9.2.3 NHC-catalyzed acylations
9.3 Electrophilic carbon-centered radicals
9.3.1 Secondary amine-catalyzed α-alkylation of aldehydes
9.3.2 Palladium-catalyzed C-H arylation
9.3.3 Copper-catalyzed trifluoromethylation of aryl boronic acids
9.4 Conclusion
9.5 References
10 Photoredox catalyzed α-functionalization of amines – Visible light
mediated carbon-carbon and carbon-hetero bond forming
reactions
10.1 Introduction
10.2 Aza-Henry Reaction
10.3 Addition of malonates
10.4 Mannich reaction
10.5 Allylation
10.6 Cyanation of tertiary amines
10.7 Alkynylation
10.8 [3+2] cycloaddition reaction
10.9 Acylation
10.10 C-heteroatom (C–P, C–O, C–N) bond formation
10.11 Conclusion
10.12 References
11 Metal complexes for photohydrogenation and hydrogen evolution
11.1 Analysis of construction components of artificial photocatalytic
systems
11.1.1 Chromophore
11.1.2 Electron relay
11.1.3 Redox equivalents
11.1.4 Reduction catalysts
11.1.5 Intramolecular hydrogen evolving photocatalysts
11.1.6 Oxidation catalysts
11.1.7 Intramolecular oxidation catalysts
11.1.8 Comparison of inter- and intramolecular photocatalysis
11.2 Intramolecular photocatalysts for hydrogen production
and hydrogenation
11.2.1 Hydrogen production
11.2.2 Photohydrogenation
11.2.3 Photophysics
11.2.4 Ru(tpphz)Pd-type catalysts as photochemical molecular
devices (PMD)
11.3 Conclusion
11.4 References
12 Heterogeneous semiconductor photocatalysis
12.1 Inorganic semiconductors
12.1.1 General features of a photocatalyst
12.1.1.1 Band structure and band gap
12.1.1.2 The Fermi level and charge separation
12.1.2 How to tune a photocatalyst
12.1.2.1 Doping and Co-Catalysts
12.1.2.2 Particle size effect
12.1.3 Selected examples of photocatalysts and their application to
organic synthesis
12.1.3.1 TiO2 – an UV active photocatalyst | 221
12.1.3.2 Selected examples of visible light active photocatalysts
12.2 Organic semiconductors
12.2.1 Basic properties of organic semiconductors
12.2.1.1 Band structure and band gap
12.2.1.2 Photoinduced electron transfer – Exciton generation and
dissociation
12.2.2 Application of conjugated polymers in photocatalysis
12.2.2.1 Linear conjugated polymers
12.2.2.2 Conjugated polymers with layered structure
12.3 References
13 Polyoxometalates in photocatalysis
13.1 Introduction
13.1.1 Polyoxometalates – Molecular metal oxide clusters
13.1.2 Concepts in polyoxometalate photochemistry
13.1.3 The basics of POM photochemistry
13.1.4 Traditional photooxidation of organic substrates
13.2 Recent developments in POM photochemistry
13.2.1 Water oxidation by Ru- and Co-polyoxometalates
13.2.2 Polyoxoniobate water oxidation
13.2.3 Water oxidation by Dawson anions in ionic liquids
13.2.4 Photoreductive CO2-activation
13.2.5 Photoreductive H2 generation
13.3 Optimizing photocatalytic performance of polyoxometalates
13.3.1 Structurally adaptive systems
13.3.2 Optimized photoactivity by metal substitution
13.3.3 Inspiration from the solid-state world
13.4 Conclusion
13.5 Acknowledgments
13.6 References
14 Description of excited states in photocatalysis with theoretical
methods
14.1 Introduction
14.2 The concept of potential energy surfaces
14.3 Computational methods for excited states
14.3.1 QM-Methods
14.3.1.1 Time-dependent coupled cluster response
14.3.1.2 Time-dependent density functional theory
14.3.2 Solvent description via the QM/MM approach
14.3.2.1 MM methods
14.3.2.2 QM/MM coupling
14.4 Procedure
14.5 Examples
14.5.1 Roseoflavin
14.5.2 Benzophenone in dinucleotides
14.6 Conclusion
14.7 References
15 Transient Absorption
16 Time resolved spectroscopy in photocatalysis
Index
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