Visible-light photoredox catalysis.

In the last few years, visible-light initiated organic transformations have attracted increasing attention. The development of visible-light-promoted photocatalytic reactions, which enable rapid and efficient synthesis of fine chemicals, is highly desirable from the viewpoint of cost, safety, availability, and environmental friendliness. In this Minireview, recent advances made in this fast developing area of research are discussed.

[1]  Angelo Albini,et al.  Photocatalysis for the formation of the C-C bond. , 2007, Chemical reviews.

[2]  Durga Prasad Hari,et al.  Metal-free, visible-light-mediated direct C-H arylation of heteroarenes with aryl diazonium salts. , 2012, Journal of the American Chemical Society.

[3]  K. Zeitler,et al.  Metal-free, cooperative asymmetric organophotoredox catalysis with visible light. , 2011, Angewandte Chemie.

[4]  Mingzhao Zhu,et al.  Intermolecular [3+2] cycloaddition of cyclopropylamines with olefins by visible-light photocatalysis. , 2012, Angewandte Chemie.

[5]  Angelo Albini,et al.  Photocatalysis. A multi-faceted concept for green chemistry. , 2009, Chemical Society reviews.

[6]  D. MacMillan,et al.  Photoredox catalysis: a mild, operationally simple approach to the synthesis of α-trifluoromethyl carbonyl compounds. , 2011, Angewandte Chemie.

[7]  Juana Du,et al.  Crossed intermolecular [2+2] cycloadditions of acyclic enones via visible light photocatalysis. , 2009, Journal of the American Chemical Society.

[8]  I. Willner,et al.  Photochemical and chemical reduction of vicinal dibromides via phase transfer of 4,4'-bipyridinium radical: the role of radical disproportionation , 1983 .

[9]  B. König,et al.  Metallfreie kooperative asymmetrische Organophotoredoxkatalyse mit sichtbarem Licht , 2011 .

[10]  Rebecca L. Davis,et al.  Highly efficient aerobic oxidative hydroxylation of arylboronic acids: photoredox catalysis using visible light. , 2012, Angewandte Chemie.

[11]  Joseph W Tucker,et al.  Oxidative photoredox catalysis: mild and selective deprotection of PMB ethers mediated by visible light. , 2011, Chemical communications.

[12]  S. Fukuzumi,et al.  Photocatalytic reduction of phenacyl halides by 9,10-dihydro-10-methylacridine: control between the reductive and oxidative quenching pathways of tris(bipyridine)ruthenium complex utilizing an acid catalysis , 1990 .

[13]  Oliver Reiser,et al.  Visible light photoredox catalysis: generation and addition of N-aryltetrahydroisoquinoline-derived α-amino radicals to Michael acceptors. , 2012, Organic letters.

[14]  Corey R J Stephenson,et al.  Electron transfer photoredox catalysis: intramolecular radical addition to indoles and pyrroles. , 2010, Organic letters.

[15]  Magnus Rueping,et al.  Visible-light photoredox catalyzed oxidative Strecker reaction. , 2011, Chemical communications.

[16]  W. Xiao,et al.  Visible-light-induced oxidation/[3+2] cycloaddition/oxidative aromatization sequence: a photocatalytic strategy to construct pyrrolo[2,1-a]isoquinolines. , 2011, Angewandte Chemie.

[17]  D. Barton,et al.  Ru(bpy)32+-mediated addition of Se-phenyl p-tolueneselenosulfonate to electron rich olefins , 1994 .

[18]  A. Deronzier,et al.  Photo-oxidation of some carbinols by the Ru(II) polypyridyl complex-aryl diazonium salt system , 1984 .

[19]  Mark E. Scott,et al.  Enantioselective alpha-trifluoromethylation of aldehydes via photoredox organocatalysis. , 2009, Journal of the American Chemical Society.

[20]  Joseph W Tucker,et al.  Electron-transfer photoredox catalysis: development of a tin-free reductive dehalogenation reaction. , 2009, Journal of the American Chemical Society.

[21]  I. Willner,et al.  Solar light induced formation of chiral 2-butanol in an enzyme-catalyzed chemical system , 1984 .

[22]  C. Stephenson,et al.  Tandem visible light-mediated radical cyclization-divinylcyclopropane rearrangement to tricyclic pyrrolidinones. , 2011, Organic letters.

[23]  G. Pandey,et al.  Designing Photosystems for Harvesting Photons into Electrons by Sequential Electron-Transfer Processes: Reversing the Reactivity Profiles of α,β-Unsaturated Ketones as Carbon Radical Precursor by One Electron Reductive β-Activation , 1997 .

[24]  I. Willner,et al.  Application of multielectron charge relays in chemical and photochemical debromination processes. The role of induced disproportionation of N,N'-dioctyl-4,4'-bipyridinium radical cation in two-phase systems , 1984 .

[25]  M. A. Ischay,et al.  Visible light photocatalysis as a greener approach to photochemical synthesis. , 2010, Nature chemistry.

[26]  S. Bertrand,et al.  Highly Efficient and Stereoselective Radical Addition of Tertiary Amines to Electron‐Deficient Alkenes − Application to the Enantioselective Synthesis of Necine Bases , 2000 .

[27]  Yoshihiro Miyake,et al.  Visible-light-mediated utilization of α-aminoalkyl radicals: addition to electron-deficient alkenes using photoredox catalysts. , 2012, Journal of the American Chemical Society.

[28]  Laura Furst,et al.  Total synthesis of (+)-gliocladin C enabled by visible-light photoredox catalysis. , 2011, Angewandte Chemie.

[29]  U. Yoon,et al.  The synthetic potential of phthalimide SET photochemistry. , 2001, Accounts of chemical research.

[30]  W. Xiao,et al.  Visible light-induced intramolecular cyclization reactions of diamines: a new strategy to construct tetrahydroimidazoles. , 2011, Chemical communications.

[31]  M. Fagnoni,et al.  (Sensitized) photolysis of diazonium salts as a mild general method for the generation of aryl cations. Chemoselectivity of the singlet and triplet 4-substituted phenyl cations. , 2005, The Journal of organic chemistry.

[32]  A. Deronzier,et al.  Photo-oxidation of tris(2,2′-bipyridine)ruthenium(II) by para-substituted benzene diazonium salts in acetonitrile. Two-compartment photoelectrochemical cell applications , 1984 .

[33]  R. S. Andrews,et al.  Investigating the rate of photoreductive glucosyl radical generation. , 2011, Organic letters.

[34]  G. Pandey,et al.  Photoinduced set generation of α-amineradicals : A practical method for the synthesis of pyrrolidines and piperidines , 1989 .

[35]  Wei Yu,et al.  Synthesis of oxindoles via visible light photoredox catalysis. , 2012, Organic & biomolecular chemistry.

[36]  R. Kellogg,et al.  CHEMISTRY OF DIHYDROPYRIDINES .9. HYDRIDE TRANSFER FROM 1,4-DIHYDROPYRIDINES TO SP3-HYBRIDIZED CARBON IN SULFONIUM SALTS AND ACTIVATED HALIDES - STUDIES WITH NAD(P)H MODELS , 1979 .

[37]  G. Pandey,et al.  Visible Light Initiated Photosensitized Electron Transfer Cyclizations of Aldehydes and Ketones to Tethered α,β-Unsaturated Esters: Stereoselective Synthesis of Optically Pure C-Furanosides† , 1997 .

[38]  Megan A. Cismesia,et al.  Visible Light Photocatalysis of Radical Anion Hetero-Diels-Alder Cycloadditions. , 2011, Tetrahedron.

[39]  J. Borak,et al.  A new photolabile protecting group for release of carboxylic acids by visible-light-induced direct and mediated electron transfer. , 2009, The Journal of organic chemistry.

[40]  Carlos Vila,et al.  Dual catalysis: combining photoredox and Lewis base catalysis for direct Mannich reactions. , 2011, Chemical communications.

[41]  M. Akita,et al.  Photo-activation of Pd-catalyzed Sonogashira coupling using a Ru/bipyridine complex as energy transfer agent. , 2007, Dalton transactions.

[42]  G. Masson,et al.  Photoredox-initiated α-alkylation of imines through a three-component radical/cationic reaction. , 2012, Chemistry.

[43]  C. Tung,et al.  Reactivity and mechanistic insight into visible-light-induced aerobic cross-dehydrogenative coupling reaction by organophotocatalysts. , 2012, Chemistry.

[44]  S. Marinković,et al.  Thiocarbonyl compounds as regulating reagent in the radical addition of tertiary amines with alkenes using photoelectron transfer conditions. , 2006, Organic & biomolecular chemistry.

[45]  Wei Xu,et al.  Single electron transfer promoted photocyclization reactions of (aminoalkyl)cyclohexenones. Mechanistic and synthetic features of processes involving the generation and reactions of amine cation and .alpha.-amino radicals , 1991 .

[46]  Melanie S. Sanford,et al.  Room-temperature C-H arylation: merger of Pd-catalyzed C-H functionalization and visible-light photocatalysis. , 2011, Journal of the American Chemical Society.

[47]  A. Deronzier,et al.  Photocatalysis of the Pschorr reaction by tris-(2,2′-bipyridyl)ruthenium(II) in the phenanthrene series , 1984 .

[48]  O. Ishitani,et al.  Redox-photosensitized reactions. 13. Ru(bpy)32+-photosensitized reactions of an NADH model, 1-benzyl-1,4-dihydronicotinamide, with aromatic carbonyl compounds and comparison with thermal reactions , 1987 .

[49]  David C. Fabry,et al.  Light-mediated heterogeneous cross dehydrogenative coupling reactions: metal oxides as efficient, recyclable, photoredox catalysts in C-C bond-forming reactions. , 2012, Chemistry.

[50]  I. Willner,et al.  Photocatalyzed and electrocatalyzed reduction of vic-dibromides and activated ketones using ruthenium(I) tris(bipyridine) as electron-transfer mediator , 1990 .

[51]  Corey R J Stephenson,et al.  Intermolecular atom transfer radical addition to olefins mediated by oxidative quenching of photoredox catalysts. , 2011, Journal of the American Chemical Society.

[52]  C. Stephenson,et al.  Visible-light photoredox catalysis: aza-Henry reactions via C-H functionalization. , 2010, Journal of the American Chemical Society.

[53]  S. Usui,et al.  A novel photocatalytic asymmetric synthesis of (R)-(+)-1,1′-bi-2-naphthol derivatives by oxidative coupling of 3-substituted-2-naphthol with Δ-[Ru(menbpy)3]2+[menbpy = 4,4′-di(1R,2S,5R)-(–)-menthoxycarbonyl-2,2′-bipyridine], which posseses molecular helicity , 1993 .

[54]  M. Oda,et al.  Reductive decarboxylation of N-(acyloxy)phthalimides via redox-initiated radical chain mechanism , 1992 .

[55]  Christopher K Prier,et al.  Discovery of an α-Amino C–H Arylation Reaction Using the Strategy of Accelerated Serendipity , 2011, Science.

[56]  R. S. Andrews,et al.  Intermolecular addition of glycosyl halides to alkenes mediated by visible light. , 2010, Angewandte Chemie.

[57]  A. Yamaguchi,et al.  Photoinduced electron-transfer systems consisting of electron-donating pyrenes or anthracenes and benzimidazolines for reductive transformation of carbonyl compounds , 2006 .

[58]  O. Ishitani,et al.  Redox-photosensitized reactions. 11. Ru(bpy)32+-photosensitized reactions of 1-benzyl-1,4-dihydronicotinamide with aryl-substituted enones, derivatives of methyl cinnamate, and substituted cinnamonitriles: electron-transfer mechanism and structure-reactivity relationships , 1984 .

[59]  Magnus Rueping,et al.  Photoredox catalyzed C-P bond forming reactions-visible light mediated oxidative phosphonylations of amines. , 2011, Chemical communications.

[60]  E. Doris,et al.  Cp2TiCl-mediated selective reduction of alpha,beta-epoxy ketones. , 2001, The Journal of organic chemistry.

[61]  R. Kellogg,et al.  Light induced and dye accelerated reductions of phenacyl onium salts by 1,4-dihydropyridines , 1978 .

[62]  Steen Rasmussen,et al.  Nucleobase mediated, photocatalytic vesicle formation from an ester precursor. , 2009, Journal of the American Chemical Society.

[63]  F. Teplý.  Photoredox catalysis by [Ru(bpy)3]2+ to trigger transformations of organic molecules. Organic synthesis using visible-light photocatalysis and its 20th century roots , 2011 .

[64]  Joseph W Tucker,et al.  Tin-free radical cyclization reactions initiated by visible light photoredox catalysis. , 2010, Chemical communications.

[65]  G. Pandey,et al.  A Novel Photosystem for Harvesting Visible Light to Drive Photoinduced Electron Transfer (PET) Reductions: β‐Activation of α, β‐Unsaturated Ketones for Radical Cyclizations , 1994 .

[66]  C. G. Fry,et al.  Radical cation Diels-Alder cycloadditions by visible light photocatalysis. , 2011, Journal of the American Chemical Society.

[67]  R. Kellogg,et al.  3-Methyl-2,3-dihydrobenzothiazoles as reducing agents. Dye enhanced photoreactions , 1985 .

[68]  Shunichi Fukuzumi,et al.  Tris(bipyridyl)ruthenium(II)-photosensitized reaction of 1-benzyl-1,4-dihydronicotinamide with benzyl bromide , 1984 .

[69]  T. Yoon,et al.  [3+2] cycloadditions of aryl cyclopropyl ketones by visible light photocatalysis. , 2011, Journal of the American Chemical Society.

[70]  T. Poisson,et al.  Visible light mediated azomethine ylide formation-photoredox catalyzed [3+2] cycloadditions. , 2011, Chemical communications.

[71]  T. Hirao,et al.  Ruthenium–Bipyridine Complex-Catalyzed Photo-Induced Reduction of Nitrobenzenes with Hydrazine , 2004 .

[72]  Jyh-Myng Zen,et al.  An efficient and selective photocatalytic system for the oxidation of sulfides to sulfoxides. , 2003, Angewandte Chemie.

[73]  L. Zhang,et al.  Utilization of natural sunlight and air in the aerobic oxidation of benzyl halides. , 2011, Organic letters.

[74]  David A. Nicewicz,et al.  Merging Photoredox Catalysis with Organocatalysis: The Direct Asymmetric Alkylation of Aldehydes , 2008, Science.

[75]  D. MacMillan,et al.  Trifluoromethylation of arenes and heteroarenes by means of photoredox catalysis , 2011, Nature.

[76]  K. Zeitler.  Photoredox catalysis with visible light. , 2009, Angewandte Chemie.

[77]  S. Bertrand,et al.  Highly efficient photochemical addition of tertiary amines to electron deficient alkenes. Diastereoselective addition to (5R)-5-menthyloxy-2[5H]-furanone , 1999 .

[78]  O. Ishitani,et al.  Formation of a novel type of adduct between an NADH model and carbonyl compounds by photosensitization using Ru(bpy)32+1 , 1983 .

[79]  K. Loh,et al.  Graphene oxide and Rose Bengal: oxidative C–H functionalisation of tertiary amines using visible light , 2011 .

[80]  M. Yasuda,et al.  Tris(2,2'-bipyridine)ruthenium(2+)-mediated photoreduction of olefins with 1-benzyl-1,4-dihydronicotinamide: a mechanistic probe for electron-transfer reactions of NAD(P)H-model compounds , 1981 .

[81]  Pixu Li,et al.  Aerobic visible-light photoredox radical C-H functionalization: catalytic synthesis of 2-substituted benzothiazoles. , 2012, Organic letters.

[82]  Corey R J Stephenson,et al.  Functionally diverse nucleophilic trapping of iminium intermediates generated utilizing visible light. , 2012, Organic letters.

[83]  M. A. Ischay,et al.  [2+2] cycloadditions by oxidative visible light photocatalysis. , 2010, Journal of the American Chemical Society.

[84]  G. Pandey,et al.  A new strategy for the construction of carbo- and oxycycles by intramolecular reductive coupling of α,β-unsaturated esters , 1998 .

[85]  D. MacMillan,et al.  Enantioselective α-benzylation of aldehydes via photoredox organocatalysis. , 2010, Journal of the American Chemical Society.

[86]  I. Guzei,et al.  Photocatalytic Reductive Cyclizations of Enones: Divergent Reactivity of Photogenerated Radical and Radical Anion Intermediates. , 2011, Chemical science.

[87]  Jakob Wirz,et al.  Photoremovable protecting groups: reaction mechanisms and applications , 2002, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.

[88]  Suresh Das,et al.  Photocatalyzed multiple additions of amines to {alpha}, {beta}-unsaturated esters and nitriles , 1994 .

[89]  Kirsten Zeitler.  Photoredoxkatalyse mit sichtbarem Licht , 2009 .

[90]  G. Pandey,et al.  Ein neues Photosystem zur Anregung von Elektronentransfer-Reduktionen mit sichtbarem Licht: β-Aktivierung von α,ß-ungesättigten Ketonen für radikalische Cyclisierungen† , 1994 .

[91]  M. Akita,et al.  Photoinduced Oxyamination of Enamines and Aldehydes with TEMPO Catalyzed by [Ru(bpy)3]2+ , 2009 .

[92]  M. Oda,et al.  Redox-Mediated Decarboxylative Photo-Phenylselenenylation of N-Acyloxyphthalimides , 1993 .

[93]  Jagan M. R. Narayanam,et al.  Visible-light-mediated conversion of alcohols to halides. , 2011, Nature chemistry.

[94]  Laura Furst,et al.  Visible light-mediated intermolecular C-H functionalization of electron-rich heterocycles with malonates. , 2010, Organic letters.

[95]  Durga Prasad Hari,et al.  Eosin Y catalyzed visible light oxidative C-C and C-P bond formation. , 2011, Organic letters.

[96]  Visible-light photoredox catalysis: dehalogenation of vicinal dibromo-, α-halo-, and α,α-dibromocarbonyl compounds. , 2011, The Journal of organic chemistry.

[97]  M. A. Ischay,et al.  Efficient visible light photocatalysis of [2+2] enone cycloadditions. , 2008, Journal of the American Chemical Society.

[98]  G. Sammis,et al.  Photoinduced electron-transfer-promoted redox fragmentation of N-alkoxyphthalimides. , 2011, Organic letters.

[99]  J. Pinson,et al.  Covalent Modification of Carbon Surfaces by Aryl Radicals Generated from the Electrochemical Reduction of Diazonium Salts , 1997 .

[100]  M. Oda,et al.  Photosensitized decarboxylative Michael addition through N-(acyloxy)phthalimides via an electron-transfer mechanism , 1991 .

[101]  Corey R J Stephenson,et al.  Visible light photoredox catalysis: applications in organic synthesis. , 2011, Chemical Society reviews.

[102]  L. Fensterbank,et al.  Visible-light-induced photoreductive generation of radicals from epoxides and aziridines. , 2011, Angewandte Chemie.

[103]  C. Galli.  Radical reactions of arenediazonium ions: An easy entry into the chemistry of the aryl radical , 1988 .

[104]  T. Yoon,et al.  Photocatalytic [2 + 2] cycloadditions of enones with cleavable redox auxiliaries. , 2012, Organic letters.

[105]  G. Ciamician,et al.  THE PHOTOCHEMISTRY OF THE FUTURE. , 1912, Science.

[106]  C. Stephenson,et al.  Shining light on photoredox catalysis: theory and synthetic applications. , 2012, The Journal of organic chemistry.

[107]  B. Ferrer,et al.  A photocatalytic acid- and base-free Meerwein-Ponndorf-Verley-type reduction using a [Ru(bpy)3]2+/viologen couple. , 2006, Chemistry.