Pt(ii) coordination complexes as visible light photocatalysts for the oxidation of sulfides using batch and flow processes.

A new catalytic system for the photooxidation of sulfides based on Pt(ii) complexes is presented. The catalyst is capable of oxidizing a large number of sulfides containing aryl, alkyl, allyl, benzyl, as well as more complex structures such as heterocycles and methionine amino acid, with complete chemoselectivity. In addition, the first sulfur oxidation in a continuous flow process has been developed.

[1]  F. Dumur,et al.  Visible‐light‐sensitive photoredox catalysis by iron complexes: Applications in cationic and radical polymerization reactions , 2016 .

[2]  J. Xie,et al.  Gold-Catalyzed Highly Selective Photoredox C(sp(2) )-H Difluoroalkylation and Perfluoroalkylation of Hydrazones. , 2016, Angewandte Chemie.

[3]  P. Ceroni,et al.  Organocatalytic Enantioselective Alkylation of Aldehydes with [Fe(bpy)3]Br2 Catalyst and Visible Light , 2015 .

[4]  T. McCallum,et al.  Indole Functionalization via Photoredox Gold Catalysis. , 2015, Organic letters.

[5]  K. Ohkubo,et al.  Mechanisms and applications of cyclometalated Pt( II ) complexes in photoredox catalytic tri fl uoromethylation , 2015 .

[6]  O. Reiser,et al.  Copper in Photocatalysis , 2014 .

[7]  Volker Hessel,et al.  Photochemical transformations accelerated in continuous-flow reactors: basic concepts and applications. , 2014, Chemistry.

[8]  Burkhard König,et al.  Synthetic applications of eosin Y in photoredox catalysis. , 2014, Chemical communications.

[9]  Corey R J Stephenson,et al.  The Development of Visible-Light Photoredox Catalysis in Flow. , 2014, Israel journal of chemistry.

[10]  J. Padrón,et al.  Novel clioquinol and its analogous platinum complexes: importance, role of the halogen substitution and the hydroxyl group of the ligand. , 2013, Dalton transactions.

[11]  L. Fensterbank,et al.  Aryl radical formation by copper(I) photocatalyzed reduction of diaryliodonium salts: NMR evidence for a Cu(II)/Cu(I) mechanism. , 2013, Chemistry.

[12]  D. MacMillan,et al.  Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis. , 2013, Chemical reviews.

[13]  C. Tung,et al.  A highly efficient and selective aerobic cross-dehydrogenative-coupling reaction photocatalyzed by a platinum(II) terpyridyl complex. , 2013, Chemistry.

[14]  A. Maguire,et al.  Asymmetric oxidation of sulfides , 2013 .

[15]  J. Xie,et al.  Highly efficient visible-light-induced aerobic oxidative C-C, C-P coupling from C-H bonds catalyzed by a gold(III)-complex. , 2013, Organic & biomolecular chemistry.

[16]  Qi Yang,et al.  A simple metal-free catalytic sulfoxidation under visible light and air , 2013 .

[17]  K. Ohkubo,et al.  Selective photocatalytic reactions with organic photocatalysts , 2013 .

[18]  Lei Shi,et al.  Photoredox functionalization of C-H bonds adjacent to a nitrogen atom. , 2012, Chemical Society reviews.

[19]  Zhenghong Lu,et al.  Highly efficient blue phosphorescence from triarylboron-functionalized platinum(II) complexes of N-heterocyclic carbenes. , 2012, Journal of the American Chemical Society.

[20]  Jitka Daďová,et al.  Photooxidation of Sulfides to Sulfoxides Mediated by Tetra‐O‐Acetylriboflavin and Visible Light , 2012 .

[21]  Xiang Zhao,et al.  Theoretical investigation on quinoline-based platinum (II) complexes as efficient singlet oxygen photosensitizers in photodynamic therapy , 2011 .

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

[23]  C. Chatgilialoglu,et al.  Radiation chemical studies of methionine in aqueous solution: understanding the role of molecular oxygen. , 2010, Chemical research in toxicology.

[24]  Gloria Hernández-Torres,et al.  Enantiopure sulfoxides: recent applications in asymmetric synthesis. , 2009, Chemical communications.

[25]  J. Williams,et al.  Optimising the luminescence of platinum(II) complexes and their application in organic light emitting devices (OLEDs) , 2008 .

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

[27]  H. Adams,et al.  Deep-red luminescence and efficient singlet oxygen generation by cyclometalated platinum(II) complexes with 8-hydroxyquinolines and quinoline-8-thiol. , 2006, Inorganic chemistry.

[28]  I. Manet,et al.  Photosensitized oxidation of sulfides: discriminating between the singlet-oxygen mechanism and electron transfer involving superoxide anion or molecular oxygen. , 2006, Chemistry.

[29]  A. Yamagishi,et al.  Enantioselective photooxidation of a sulfide by a chiral ruthenium(II) complex immobilized on a montmorillonite clay surface: the role of weak interactions in asymmetric induction. , 2006, The journal of physical chemistry. B.

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

[31]  A. Yamagishi,et al.  Production of an optically active sulfoxide by use of colloidally dispersed .LAMBDA.-tris(2,2'-bipyridyl)ruthenium(II) montmorillonite as a photosensitizer , 1989 .

[32]  J. Senn‐Bilfinger,et al.  (H+-K+)-ATPase inhibiting 2-[(2-pyridylmethyl)sulfinyl]benzimidazoles. 2. The reaction cascade induced by treatment with acids. Formation of 5H-pyrido[1',2':4,5][1,2,4]thiadiazino[2,3-a]benzimidazol-13-ium salts and their reactions with thiols , 1987 .