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Review
. 2013 Jul 10;113(7):5322-63.
doi: 10.1021/cr300503r. Epub 2013 Mar 19.

Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis

Christopher K Prier  1 , Danica A Rankic, David W C MacMillan
Affiliations
Review

Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis

Christopher K Prier et al. Chem Rev. .
No abstract available

PubMed Disclaimer

Figures

Figure 1
Figure 1
Ruthenium polypyridyl complexes: versatile visible light photocatalysts.
Figure 2
Figure 2
Fluorescence quenching (Stern–Volmer) studies.
Figure 3
Figure 3
Enantiomeric forms of Ru(bpy)32+.
Figure 4
Figure 4
Photocatalysts employed in arene trifluoromethylation.
Scheme 1
Scheme 1
Simplified Molecular Orbital Depiction of Ru(bpy)32+ Photochemistry
Scheme 2
Scheme 2
Oxidative and Reductive Quenching Cycle of Ru(bpy)32+
Scheme 3
Scheme 3
Photoredox Reduction of Electron-Deficient Olefins
Scheme 4
Scheme 4
Reductive Dehalogenation of Phenacyl Bromides
Scheme 5
Scheme 5
Reductive Dimerization of Benzyl Bromide
Scheme 6
Scheme 6
Reductive Dimerization of 4-Nitrobenzyl Bromide by Cu(dap)2+
Scheme 7
Scheme 7
Stephenson's Photoredox Reductive Dehalogenation
Scheme 8
Scheme 8
Reductive Dehalogenation of Alkyl, Alkenyl, and Aryl Iodides
Scheme 9
Scheme 9
Redox Chemistry of Dimethyl Viologen (MV2+)
Scheme 10
Scheme 10
Reduction of vic-Dibromides via Photoredox and Viologen Catalysis in a Biphasic System
Scheme 11
Scheme 11
Enzymatic Regeneration of NADH Coupled with the Photoredox Reductive Dehalogenation of vic-Dibromides
Scheme 12
Scheme 12
Photoredox Reduction of Phenacylsulfonium Salts
Scheme 13
Scheme 13
Reduction of Hydrazides and Hydrazines Using Ru(bpz)32+
Scheme 14
Scheme 14
Photoredox-Catalyzed Reductive Radical Cyclization
Scheme 15
Scheme 15
Radical Cyclizations of Alkyl, Alkenyl, and Aryl Iodides
Scheme 16
Scheme 16
Cascade Photoredox Cyclization Reactions
Scheme 17
Scheme 17
Reductive Opening of Epoxides and Aziridines
Scheme 18
Scheme 18
Tandem Ring-Opening/Allylation of α-Ketoepoxides
Scheme 19
Scheme 19
N-(Acyloxy)phthalimides as Masking Groups for Alkyl Radicals
Scheme 20
Scheme 20
Reductive Cleavage of the N-Methylpicolinium Group
Scheme 21
Scheme 21
N-Alkoxyphthalimides as Masking Groups for Aldehydes
Scheme 22
Scheme 22
Oxidation of Benzylic Alcohols to Aldehydes
Scheme 23
Scheme 23
Aerobic Oxidation of Benzylic Halides
Scheme 24
Scheme 24
Aerobic Oxidative Hydroxylation of Arylboronic Acids
Scheme 25
Scheme 25
Oxidative Conversion of Thiobenzanilides to Benzothiazoles
Scheme 26
Scheme 26
Oxidative Deprotection of para-Methoxybenzyl Ethers
Scheme 27
Scheme 27
Oxidative Biaryl Coupling with a Chiral Photocatalyst
Scheme 28
Scheme 28
Pathways of Amine Oxidation to Iminium Ions
Scheme 29
Scheme 29
Photoredox aza-Henry Reaction via Iminium Intermediate
Scheme 30
Scheme 30
Trapping of Photoredox-Generated Iminium Ions with Diverse Nucleophiles
Scheme 31
Scheme 31
Synthesis of Tetrahydroimidazoles via Intramolecular Trapping of a Photoredox-Generated Iminium Ion
Scheme 32
Scheme 32
α-Arylation of Amides via Hydrogen Atom Abstraction
Scheme 33
Scheme 33
Rovis's Merger of Photoredox Catalysis with N-Heterocyclic Carbene Catalysis: The α-Acylation of Amines
Scheme 34
Scheme 34
Photoredox-Promoted Azomethine Ylide [3 + 2] Cycloadditions
Scheme 35
Scheme 35
Cyclization of Aminium Radical Cations
Scheme 36
Scheme 36
Generic Atom Transfer Radical Addition (ATRA) Cycle
Scheme 37
Scheme 37
Atom Transfer Radical Addition of Se-Phenyl p-Tolueneselenosulfonate to Alkyl Vinyl Ethers
Scheme 38
Scheme 38
Photoredox Atom Transfer Radical Addition (ATRA)
Scheme 39
Scheme 39
Mechanism of the Photoredox ATRA
Scheme 40
Scheme 40
Merger of Photoredox Catalysis and Enamine Catalysis: The Asymmetric α-Alkylation of Aldehydes
Scheme 41
Scheme 41
Enantioselective α-Alkylation of Aldehydes via Photoredox Organocatalysis
Scheme 42
Scheme 42
α-Trifluoromethylation of Aldehydes
Scheme 43
Scheme 43
α-Benzylation of Aldehydes via Photoredox Organocatalysis
Scheme 44
Scheme 44
Eosin Y-Catalyzed Photoredox Organocatalysis
Scheme 45
Scheme 45
Photoredox-Catalyzed Pschorr Reaction
Scheme 46
Scheme 46
Arylation of Heterocycles with Diazonium Salts
Scheme 47
Scheme 47
Pd-Catalyzed C–H Functionalization and Arylation
Scheme 48
Scheme 48
Merger of Palladium and Photoredox Catalysis in C–H Arylation with Aryldiazonium Salts
Scheme 49
Scheme 49
Malonyl Radical Additions to Electron-Rich Heterocycles
Scheme 50
Scheme 50
Photoredox Catalysis in the Total Synthesis of Gliocladin C
Scheme 51
Scheme 51
Photoredox Arene and Heteroarene Trifluoromethylation
Scheme 52
Scheme 52
Photoredox Trifluoromethylation of Lipitor
Scheme 53
Scheme 53
Merger of Photoredox and High-Valent Copper Catalysis: Trifluoromethylation of Arylboronic Acids
Scheme 54
Scheme 54
Arylation Reactions of Styrenes and Enol Acetates
Scheme 55
Scheme 55
α-Trifluoromethylation of Ketones, Esters, and Amides
Scheme 56
Scheme 56
Photoredox Oxytrifluoromethylation of Styrenes
Scheme 57
Scheme 57
Photoredox α-Allylation of α-Halocarbonyls
Scheme 58
Scheme 58
Oxidative Coupling of Enamines with Enolsilanes
Scheme 59
Scheme 59
α-Oxyamination of Aldehydes with TEMPO
Scheme 60
Scheme 60
Yoon's Photoredox Enone [2 + 2] Cycloaddition
Scheme 61
Scheme 61
Crossed Intermolecular [2 + 2] Cycloadditions
Scheme 62
Scheme 62
Use of the N-Methylimidazolyl Group as a Redox Auxiliary
Scheme 63
Scheme 63
Photoredox Reductive Cyclization of Bis(enones)
Scheme 64
Scheme 64
Reductive Cyclization of Chalcones to Cyclopentanols
Scheme 65
Scheme 65
[2 + 2] Cycloaddition of Electron-Rich Bis(styrenes)
Scheme 66
Scheme 66
Ru(bpm)32+-Catalyzed Intermolecular [2 + 2] Cycloaddition of Styrenes
Scheme 67
Scheme 67
Radical Anion Hetero-Diels–Alder Reaction of Bis(enones)
Scheme 68
Scheme 68
Radical Cation Diels–Alder Reaction
Scheme 69
Scheme 69
Total Synthesis of Heitziamide A via Photoredox Cycloaddition
Scheme 70
Scheme 70
Synthesis of Endoperoxides via [2 + 2 + 2] Cycloaddition
Scheme 71
Scheme 71
Intramolecular [3 + 2] Cycloaddition of Cyclopropyl Ketones
Scheme 72
Scheme 72
Intermolecular [3 + 2] Cycloaddition of Cyclopropylamines
Scheme 73
Scheme 73
α-Amino Radical Conjugate Addition to Michael Acceptors
Scheme 74
Scheme 74
Addition of Glycosyl Radicals to Electron-Deficient Olefins
Scheme 75
Scheme 75
Photoredox Radical Conjugate Addition Applied to the Total Synthesis of (–)-Aplyviolene
Scheme 76
Scheme 76
Photoredox α-Arylation of Amines with 1,4-Dicyanobenzene
Scheme 77
Scheme 77
Scope of the Photoredox Amine α-Arylation Reaction
Scheme 78
Scheme 78
Photoredox Hydrothiolation of Alkenes via Thiyl Radicals
Scheme 79
Scheme 79
Photoredox Generation of the Vilsmeier–Haack Reagent
Scheme 80
Scheme 80
Triplet–Triplet Energy Transfer from *Ru(bpy)32+ to Acceptor A
Scheme 81
Scheme 81
[2 + 2] Styrene Cycloadditions Enabled via Energy Transfer
Scheme 82
Scheme 82
Isomerization of trans-4-Cyanostilbene via Energy Transfer from a Ru(bpy)32+-type Ligand
Scheme 83
Scheme 83
Styrene Dimerization Catalyzed by a Bimetallic Ru/Pd Complex
Scheme 84
Scheme 84
α-Methylstyrene Dimerization by a Bimetallic Ru/Pd Complex
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