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Kankala, Shravankumar
- Serendipitous Formation of First Neutral Mononuclear Rh(II) Complex of 1, 10-Phenanthroline
Abstract Views :315 |
PDF Views:2
Authors
Shravankumar Kankala
1,
Prasad Gundepaka
2,
Vinutha Chakilam
1,
Kavitha Natte
1,
Hanmanthu Guguloth
1,
Ravinder Vadde
1,
Chandra Sekhar Vasam
3,
Mukkanti Kagga
2
Affiliations
1 Department of Chemistry, Kakatiya University, Warangal
2 Centre for Pharmaceutical Science, Institute of Science and Technology, JNTU, Hyderabad
3 Department of Chemistry, Satavahana University, Karimnagar, 505 001
1 Department of Chemistry, Kakatiya University, Warangal
2 Centre for Pharmaceutical Science, Institute of Science and Technology, JNTU, Hyderabad
3 Department of Chemistry, Satavahana University, Karimnagar, 505 001
Source
Asian Journal of Research in Chemistry, Vol 6, No 8 (2013), Pagination: 727-730Abstract
The reaction of RhCl3 with 1,10-phenanthroline followed by a carboxyl functionalized tertiaryphosphine in refluxing ethanol led to serendipitous formation of a first neutral mononuclear Rh(II) complex of 1,10-phenanthroline as [Rh(II)Cl<SUB>2</SUB>(1,10-phen)2] without incorporating the phosphine. This incident was evidenced by elemental analysis, single crystal X-ray diffraction, EPR and Mass spectroscopic studies.Keywords
Rhodium, Tertiary phosphines, 1, 10-phenanthroline, Reduction
References
- Ungváry F. Application of transition metals in hydroformylation: Annual survey covering the year 2005. Coord. Chem. Rev. 2007; 251: 2072-2086.
- Erre G, Enthaler S, Junge K, Gladiali S and Beller M. Synthesis and application of chiral monodentate phosphines in asymmetric hydrogenation. Coord. Chem. Rev. 2008; 252: 471-491.
- Shaughnessy K H. Hydrophilic Ligands and Their Application in Aqueous-Phase Metal-Catalyzed Reactions. Chem. Rev. 2009; 109: 643-710.
- Saidi O, Liu S and Xiao J. Effects of ligands on the rhodiumcatalyzed hydroformylation of acrylate. J. Mol. Cat. A Chemical. 2009; 305: 130-134.
- Barry C G, Turney E C, Day C S, Saluta G, Kucera G L and Bierbach U. Thermally Inert Metal Ammines as Light-Inducible DNA-Targeted Agents. Synthesis, Photochemistry, and Photobiology of a Prototypical Rhodium(III)-Intercalator Conjugate. Inorg. Chem. 2002; 41: 7159-7169.
- Terbrueggen R H, Johann T W and Barton J K. Functionalized Rhodium Intercalators for DNA Recognition. Inorg. Chem. 1998; 37: 6874-6883.
- Rivas A B, Pérez-Torrente J J, Pardey A J, Masdeu-Bultó A M, Diéguez M and Oro L A. Hydroformylation of oct-1-ene catalyzed by dinuclear gem-dithiolato-bridged rhodium(I) complexes and phosphorus donor ligands. J. Mol. Cat. A Chemical. 2009; 300: 121- 131.
- Toganoh M, Harada N and Furuta H. Hydrogen-bonding network in new scorpionate-type ligand composed of pyridine/pyrrole hybrid and anion-binding behavior of the corresponding rhodium complexes in alkyne cyclotrimerization reaction. J. Organomet. Chem. 2008; 693: 3141-3150.
- Schaub T, Diskin-Posner Y, Radius U and Milstein D. Synthesis, Structure, and Reactivity of Rhodium and Iridium Complexes of the Chelating Bis-Sulfoxide tBuSOC 2H 4SO tBu. Selective O-H Activation of 2-Hydroxy- isopropyl-pyridine. Inorg. Chem. 2008; 47: 6502-6512.
- Shibue M, Hirotsu M, Nishioka T and Kinoshita I. Ruthenium and Rhodium Complexes with Thiolate-Containing Pincer Ligands Produced by C-S Bond Cleavage of Pyridyl-Substituted Dibenzothiophenes. Organometallics. 2008; 27: 4475-4483.
- Blacker A J, Duckett S B, Grace J, Perutz R N and Whitwood A C. Reactivity, Structures, and NMR Spectroscopy of Half-Sandwich Pentamethylcyclopentadienyl Rhodium Amido Complexes Relevant to Transfer Hydrogenation. Organometallics. 2009; 28: 1435-1446.
- Ravinder V, Hemling H, Shumann H and Blum J. A new synthesis of hydrophilic carboxylated arylphosphines. Synth. Commun. 1992; 22: 841-851.
- Ravinder V, Hemling H, Shumann H and Blum J. A novel convenient synthesis of arylphosphines containing reactive functional groups. Synth. Commun. 1992; 22: 1453-1459.
- Schumann H, Ravindar V, Meltser L, Baidossi W, Sasson Y and Blum J. Effect of the CO2H groups of carboxylated triarylphosphines on (COD)RhCl(PAr3)-catalyzed isomerization of 1-octen-3-ol under phase transfer conditions. J. Mol. Cat. A Chemical. 1997; 118: 55-61.
- Schumann H, Hemling H, Ravindar V, Badrieh Y and Blum J. Effects of changes in the ligands on the skeleton and the catalytic activity of some new rhodium complexes with pyrazolato moieties. J. Organomet. Chem. 1994; 469: 213-219.
- Sarangapani M and Ravinder V. Reactivity of [{(6 -pcymene) RuCl(µ-Cl)}2] towards some N-heterocyclics and tertiary phosphines. Ind. J. Chem. 2002; 41(A): 2060-2064.
- Sarangapani M, Chandrasekhar V and Ravinder V. Synthesis and characterization of (6-p-cymene) RuII complexes containing N, N O donor ligands and tertiary phosphines. J. Ind. Chem. Soc. 2005; 82: 497-502.
- Usharani P, Muralidhar Reddy P, Sarangapani M and Ravinder V. Synthesis, spectral and catalytic hydrogenation studies of palladium(II) complexes containing substituted tertiary phosphines. J. Ind. Chem. Soc. 2007; 84: 122-129.
- Muralidhra Reddy P, Shanker K, Rohini R, Sarangapani M and Ravinder V. Substituted tertiary phosphine Ru(II) organometallics: Catalytic utility on the hydrolysis of etofibrate in pharmaceuticals. Spectrochim. Acta A. 2008; 70: 1231-1237.
- Chandrasekhar V, Sarangapani M, Shanker K and Ravinder V. Synthesis, characterization and hydroformylation activity of 7- azaindolate-bridged dinuclear rhodium(I)phosphines with pendant polar-groups. Appl. Organomet. Chem. 2009; 23: 460-466.
- Rosenberg B, VanCamp L and Trosko J E. Platinum compounds: a new class of potent antitumour agents. Nature. 1969; 222: 385-386.
- Scharwitz M A, Ott I, Geldmacher Y, Gust R & Sheldrick W S. Cytotoxic half-sandwich rhodium(III) complexes: Polypyridyl ligand influence on their DNA binding properties and cellular uptake. J. Organomet. Chem. 2008; 693: 2299-2309.
- Menon E L, Perera R, Navarro M, Kuhn R J & Morrison H. Phototoxicity against Tumor Cells and Sindbis Virus by an Octahedral Rhodium Bisbipyridyl Complex and Evidence for the Genome as a Target in Viral Photoinactivation. Inorg. Chem. 2004; 43: 5373-5381.
- Muir M M, Gomez G M, Muir J A and Sanchez S. Structure of trans-dibromotetrakis(pyridine)rhodium(III) bromide hexahydrate. Acta Cryst. 1987; C43: 839-842.
- Cini R, Cavaglioni A and Tiezzi E. X-ray structures of transdichloro( 4-methylpyrimidine) ( 1-phenyl)bis(pyridine)rhodium(III) hydrate and trans-dichloro(phenyl)tris(triphenylstibine)rhodium(III) ethylacetate solvate. Molecular orbital analysis of trans-dichloro (4- methylpyrimidine)( 1-phenyl)bis(pyridine)rhodium(III). Polyhedron. 1999; 18: 669-678.
- Mintert M and Sheldrick W S. Dinuclear Rh(I,I) and Rh(II,II) complexes containing bridging asymmetrically 2,7-disubstituted naphthyridines. Inorg. Chim. Acta. 1997; 254: 93-98.
- Feller M, Ben-Ari E, Gupta T, Shimon L J W, Leitus G, Diskin- Posner Y, Weiner L and Milstein D. Mononuclear Rh(II) PNP-Type Complexes. Structure and Reactivity. Inorg. Chem. 2007; 46: 10479- 10490.
- Exarchos G and Robinson S D. Observations concerning the constitution of some ‘rhodium(II) dithiocarbamato complexes’. Polyhedron. 2000; 19: 123-124.
- Willems S T H, Russcher J C, Budzelaar P H M, de Bruin B, de Gelder R, Smits J M M and Gal A W. Spontaneous disproportionation of rhodium(I) bisoxazolinates to rhodium(II). Chem. Commun. 2002; 148-149.
- JI Z, Shan Y, Guadalupe A R and Huang S D. Crystal structure of cisdichlorobis( 1,10-phenanthroline)rhodium(III) perchlorate. Zeitschrift für Kristallographie. 1999; 214: 387-388.
- Kulasingam G C, McWhinnie W R and Miller J D. The mechanism of formation and the stereochemistry of mono- and bis-complexes of rhodium(III) with 1,10-phenanthroline. J. Chem. Soc. A. 1969; 521- 524.
- Indelli M T, Carioli A and Scandola F. Excited-state absorption of tris(phenanthroline)rhodium(III). A handle on the excited-state behavior of a powerful photochemical oxidant. J. Phys. Chem. 1984; 88: 2685-2686.
- Loganathan D, Rodriguez J H and Morrison H. Photoaquation of Methylated cis-Dichlorobis(1,10-phenanthroline)rhodium(III)chloride Compounds by Direct Population of a Photoactive Triplet Excited State. J. Am. Chem. Soc. 2003; 125: 5640-5641.
- Glowiak T, Pasternak H and Pruchnik F. Structure of the binuclear rhodium(II) complex dichloro-di-µ-formato-bis(1,10-phenanthroline) dirhodium(II). Acta Cryst. 1987; C43: 1036-1038.
- Pruchnik F P, Bien M and Lachowicz T. Properties of Binuclear Rhodium(II) Complexes and Their Antibacterial Activity. Metal- Based Drugs. 1996; 3: 185-195.
- Menglet D, Bond A M, Coutinho K, Dickson R S, Lazarev G G, Olsen S A and Pilbrow J R. EPR, Electronic Spectra, and Electron Transfer Properties of the 17 Electron Carbonylhydrotris (triphenylphosphine)rhodium(II) Cation. J. Am. Chem. Soc. 1998; 120: 2086-2089.
- Vrielinck H, Callens F and Matthys P. Reinterpretation of temperature-induced dynamical behavior in the EPR spectrum of Rh2+ centers in AgCl. Physical Review B. 2003; 68: 212405.
- Sabbe K, Vrielinck H, Callens F, Boesman E, Vercammen H, Ka H, Goovaerts E, Bouwen A and Schoemaker D. Study of strongly overlapping Rh2+ EPR spectra by high-resolution magnetic resonance techniques. J. Chem. Soc. Faraday Trans. 1998; 94: 2993-2997.
- Synthesis of Piperidine Bound 3,4,5-Trisubstituted Isoxazolines Via 1,3- Dipolar Cycloaddition Reactions Catalyzed By N-Heterocyclic Carbene
Abstract Views :843 |
PDF Views:2
Authors
Prasad Gundepaka
1,
Shravankumar Kankala
2,
Hanmanthu Guguloth
2,
Shylaja Kotte
2,
Vinutha Chakilam
2,
Mukkanti Kagga
1,
Ravinder Vadde
2,
Chandra Sekhar Vasam
3
Affiliations
1 Centre for Pharmaceutical Science, Institute of Science and Technology, JNTU, Hyderabad
2 Department of Chemistry, Kakatiya University, Warangal, 506 009, IN
3 Department of Chemistry, Satavahana University, Karimnagar, 505 001, IN
1 Centre for Pharmaceutical Science, Institute of Science and Technology, JNTU, Hyderabad
2 Department of Chemistry, Kakatiya University, Warangal, 506 009, IN
3 Department of Chemistry, Satavahana University, Karimnagar, 505 001, IN
Source
Asian Journal of Research in Chemistry, Vol 6, No 10 (2013), Pagination: 916-919Abstract
A first example of organo-N-heterocyclic carbene (NHC) catalyzed click-type fast 1,3-dipolar cycloaddition of nitrile oxides with piperidine alkene alkaloids was developed for the regioselective synthesis of 3,4,5-trisubstituted isoxazolines. Triethylamine (Et3N) was employed as an effective base to generate both nitrile oxide and the organo- NHC catalyst in situ. This catalytic approach was used to attach a variety of substituents, including other biologically active fragments, onto the isoxazoline ring to selectively design multinucleus structures. A catalytic cycle is proposed and the remarkable regiocontrol in the formation of isoxazolines was ascribed to a beneficial zwitterion intermediate developed by the interaction of the strongly nucleophilic organo-NHC catalyst with alkene followed by nitrile oxide.Keywords
1,3-dipolar Cycloaddition, N-heterocyclic Carbene, Isoxazolines, Piperidine Alkene AlkaloidsReferences
- Huisgen R. 1,3-Dipolar Cycloadditions. Past and Future. Angew. Chem., Int. Ed.Engl., 1963; 2: 565-598.
- Hein J E, Fokin V V. Copper-catalyzed azide-alkyne cycloaddition (CuAAC) and beyond: new reactivity of copper(I) acetylides. Chem. Soc. Rev. 2010; 39: 1302-1315.
- Back T G, Clary K N, Gao D. Cycloadditions and Cyclizations of Acetylenic, Allenic, and Conjugated Dienyl Sulfones. Chem. Rev. 2010; 110: 4498-4553.
- Sanders B C, Friscourt F, Ledin P A, Mbua N E, Arumugam S, Guo J, Boltje T J,Popik V V, Boons G-J. Metal-free sequential [3 + 2]-dipolar cycloadditions using cyclooctynes and 1,3-dipoles of different reactivity. J. Am. Chem. Soc. 2011; 133: 949-957.
- Kissane M, Maguire A R. Asymmetric 1,3-dipolar cycloadditions of acrylamides. Chem. Soc. Rev. 2010; 39: 845- 883.
- Rück-Braun K, Freysoldt T H E, Wierschem F. 1,3-Dipolar cycloaddition on solid supports: nitrone approach towards isoxazolidines and isoxazolines and subsequent transformations. Chem. Soc. Rev. 2005; 34: 507-516.
- Scott G, Fokin V V. Ruthenium-Catalyzed Cycloaddition of Nitrile Oxides and Alkynes: Practical Synthesis of Isoxazoles. Angew. Chem. 2008; 120: 8409-8411.
- Himo F, Lovell T, Hilgraf R, Rostovtsev V V, Noodleman L, Sharpless K B,Fokin V V. Copper(I)-Catalyzed Synthesis of Azoles. DFT Study Predicts Unprecedented Reactivity and Intermediates. J. Am. Chem. Soc. 2005; 127: 210-216.
- Hansen T V, Wu P, Fokin V V. One-Pot Copper(I)-Catalyzed Synthesis of 3,5- Disubstituted Isoxazoles. J. Org. Chem. 2005; 70: 7761-7764.
- Vieira A A, Bryk F R, Conte G, Bortoluzzi A J, Gallardo H. 1,3- Dipolar cycloaddition reaction applied to synthesis of new unsymmetric liquid crystal compounds-based isoxazole. Tetrahedron Lett. 2009; 50: 905-908.
- List B. Introduction: Organocatalysis. Chem. Rev. 2007; 107: 5413.
- Bertelsen S, Jorgensen K A. Organocatalysis-after the gold rush. Chem. Soc. Rev. 2009; 38: 2178.
- Yoshida K, Furuta T, Kawabata T. Organocatalytic Chemoselective Monocylation of 1,n-Linear Diols. Angew. Chem., Int. Ed. 2011; 50: 4888-4892.
- Nair V, Pillai A N, Beneesh, P B, Suresh E. Engaging the Pyridine-DMAD Zwitterion in a Novel Strategy for the Selective Synthesis of Highly Substituted Benzene and Cyclopentenedione Derivatives. Org. Lett. 2005; 7: 4625-4628.
- Zhu X-F, Henry C E, Kwon O. Stable Tetravalent Phosphonium Enolate Zwitterions.J. Am. Chem. Soc. 2007; 129: 6722.
- Siebert M R, Yudin A K, Tantillo D J. Cycloaddition/Ring Opening Reaction Sequences of N-Alkenyl Aziridines: Influence of the Aziridine Nitrogen on Stereoselectivity. Org. Lett. 2008; 10: 57-60.
- Kankala S, Edulla R, Modem S, Vadde R, Vasam C S. NHeterocyclic carbene catalyzed intramolecular crossed aldehyde– ketone benzoin condensation in the chalcone of ophthalaldehyde: a facile synthesis of naphthalenones. Tetrahedron Lett. 2011; 52: 3828-3831.
- Breslow R. On the Mechanism of Thiamine Action. IV.1 Evidence from Studies on Model Systems. J. Am. Chem. Soc. 1958; 80: 3719-3726.
- Enders D, Niemeier O, Henseler A. Organocatalysis by NHeterocyclic Carbenes. Chem. Rev. 2007; 107: 5606-5655.
- Phillips E M, Chan A, Scheid K A. Discovering New Reactions with N-Heterocyclic Carbene Catalysis. Aldrichim. Acta. 2009; 42: 55-66.
- Bugaut X, Liu F, Glorius F. N-Heterocyclic Carbene (NHC)- Catalyzed Intermolecular Hydroacylation of Cyclopropenes. J. Am. Chem. Soc. 2011; 133: 8130.
- Kankala, S.; Vadde, R.; Vasam, C. S. N-Heterocyclic carbenecatalyzed 1,3-dipolar cycloaddition reactions: a facile synthesis of 3,5-di- and 3,4,5-trisubstituted isoxazoles. Org. Biomol. Chem. 2011; 9: 7869-7876.rhythm and reduces the force of the heart's pumping (14).