Asymmetric Synthesis Natural Product Synthesis Cross-Coupling Halogen Bond Catalysis Oxidation
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2022 | |
36.Oxygen Bridged Bimetallic [Cu-O-Se] Catalyst for Sonogashira Cross-Coupling. New. J. Chem, 2022; DOI: 10.1039/D1NJ04485K (In Press);
Santosh Kumar Sahu, Prabhupada Choudhury, Pradyota Kumar Behera, Tanmayee Bisoyi, Rashmi Ranjan Sahu, Abinash Bisoyi, Koteswara Rao Gorantla, Bhabani S. Mallik, Manoj Mohapatra, Laxmidhar Rout,*# |
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2021 | |
35.Strategy for Synthesis of Structural Analogues of Artemisinin, Resercah Journal of Berhampur University; 2021, 3, 69-82 (RJBU ISSN 2250-1681) Santosh K. Sahu, a Pradyota K. Behera, a Prabhupada Choudhury, a Madhab Chandra Maity, Papita Behera, a Amlan Swain a Raj Kiran Sahua, Subhalaxmi Panda a and Laxmidhar Rout*a,
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33.Recent advance in [3+2] cycloaddition of allene with 1,3-carbonyl ylide; Rh(II) catalyzed access to bridged polyoxocarbocyles; New. J. Chem, 2021; DOI: 10.1039/D1NJ02034J (In Press) S. K. Sahu, P. K. Behera, P. Choudhury, M. Sethi, S. Jena, and L. Rout,
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32. Oxygen bridged bimetallic CuMoO4 nanocatalyst for benzylic alcohol oxidation; mechanism and DFT study; A. J. Org. Chem. 2021, 10, 1117-1122; DOI: 10.1002/ajoc.202100192 (In Press) P. K. Behera, P. Choudhury, S K. Sahu, R. R. Sahu, A. N. Harvat, C. McNulty, A. Stitgen, J. Scanlon, M. Kar, and Prof. L. Rout
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31 Dehydrogenative oxidation of aryl methanol using oxygen bridged [Cu-O-Se] bimetallic catalyst New. J. Chem, 2021, 45, 5775-5779. https://doi.org/10.1039/D1NJ00712B P. Choudhury, P. K. Behera, S. K. Sahu, T. Bisoyi, R. R. Sahu, S. R. Prusty, A. Stitgen, J. Scanlon, Prof. L. Rout,*
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30. Recent Advances in Transition-Metal-Mediated Csp2-B and Csp2-P Cross-Coupling Reactions, Coordination Chemistry Review, 2021, 413, 213675. https://doi.org/10.1016/j.ccr.2020.213675, (Impact factor 15.5) Laxmidhar Rout and Tharmalingam Punniyamurthy,
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29.Chemotherapeutic efficacy of curcumin and resveratrol against cancer: Chemoprevention, chemoprotection, drug synergism and clinical pharmacokinetics, Seminars in Cancer Biology, 2021, 73, 310-320; https://doi.org/10.1016/j.semcancer.2020.10.010 (Impact factor 11.09) [Collaboration Paper] S. Patra; B. Pradhan; R. Nayak; C. Behera; L. Rout, M. Jena, T. Efferth, S. K. Bhutia, |
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2020 | |
28.Developments in chemistry and biological application of cotarnine & its analogs, Tetrahedron 2020, 76,50, 131663 ; https://doi.org/10.1016/j.tet.2020.131663 Sahu, S. K. Behera, P. K. Panda, S. Choudhury, P. and Rout, L
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27. Strategy and Problems for Synthesis of Antimalaria Artemisinin (Qinghaosu); Chemistry Select 2020, 29, 12333-12344 Santosh Kumar Sahu, Pradyota Kumar Behera, Prabhupada Choudhury, Subhalaxmi Panda and Laxmidhar Rout,
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26: Bimetallic BaMoO4 Nanoparticle for C-S Cross-Coupling of Thiols with Haloarene New J. Chem 2020, 44, 2500-2504 Subhalaxmi Panda, Pradyota Kumar Behera, Santosh Kumar Sahu, Reba Panigrahi, Bamakanta Garnaik and Laxmidhar Rout, https://doi.org/10.1039/C9NJ05581A |
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25: CuMoO4 Bimetallic Nanoparticles, An Efficient Catalyst for Room Temperature C-S Cross-coupling of Thiols and Haloarenes, Chemistry Eur. J. 2020, 24, 620-624 Reba Panigrahi, Santosh Kumar Sahu, Pradyota Kumar Behera, Subhalaxmi Panda, and Prof. Laxmidhar Rout, https://org/doi/10.1002/chem.201904801
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2019 | |
24: Recyclable Bimetallic CuMoO4 Nanoparticle for C-N Cross-Coupling Reaction Under Mild Condition New J. Chem 2019, 43, 19274 Reba Panigrahi, Subhalaxmi Panda, Pradyota Kumar Behera, Santosh Kumar Sahu and Dr. Laxmidhar Rout https://doi.org/10.1039/C9NJ04436A
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23: Synthesis of Acyl Derivatives of Cotarnine, Organic Synthesis Database Online, (Editor: A. S. Kendee, and J. S. Freeman) 2019, Volume 95 Dr. Laxmidhar Rout, B. B. Parida, G. Phaomei, B.Emmanuel, and Prof. A. K. Sahoo, |
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2018 | |
22: Synthesis of Acyl Derivatives of Cotarnine, Org. Syn, 2018, 95, 455. DOI: 10.15227/orgsyn.095.0455 Dr. Laxmidhar Rout, B. B. Parida, G. Phaomei, B.Emmanuel, and Prof.A. K. Sahoo,
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2017 | |
21: Metal Free Activation of C(SP3)-H Bond, Practical and Rapid Synthesis of Privileged 1-Substituted-1,2,3,4-Tetrahydroisoquinolines, Eur JOC 2017, 35, 5275-5292S. K. Choudhury, P. Rout, B. B. Parida, J-C. Florent, L. Johannes, G. Phaomei, E. Bertounesque, Prof. Laxmidhar Routhttps://doi.org/10.1002/ejoc.201700471 |
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2016 | |
20: Metal-Free Activation of a C(sp)−H Bond of Aryl Acetylenes , Chem. - A Europ. J. 2016, 22, 14812–14815,Prof. Laxmidhar Rout, Dr. Bibhuti Bhusan Parida, Dr. Jean-Claude Florent, Dr. Ludger Johannes, Santosh Kumar Choudhury, Dr. Ganngam Phaomei, Prof. Joe Scanlon and Dr. Emmanuel Bertounesquehttps://doi.org/10.1002/chem.201603003Virgin C−H bonds: The first example for activating acetylenic protons under base- and metal-free conditions is reported. This includes a general method for synthesizing propargylic derivatives of cotarnine. An array of tetrahydroisoquinolines alkaloids was synthesized by C−C bond formation between cotarnine and aryl acetylenes at room temperature. A DFT-based mechanism is proposed for the reaction. |
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19: Activation of a Carbonyl Compound by Halogen Bonding; Chem. Commun., 2014, 50, 6281-6284S. H. Jungbauer, S.M. Walter, S. Schinder, L. Rout, F. Kniep and S. M. Huberhttps://doi.org/10.1039/C4CC03124E
Halogen bond Catalysis: Using a prototypical Diels–Alder reaction as benchmark, we show that dicationic halogen-bond donors are capable of activating a neutral organic substrate. By variouscomparison experiments, the action of traces of acid or of other structural features of the halogen-bond donor not related to halogen bonding are excluded with high certainty. |
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18: Multidentate Halogen-Bond Donors as Lewis Acidic Activators or Catalysts in Halide Abstraction Reactions; Synlett, 2013, 24, 2624.
S. H. Jungbauer, F. Kniep, S.M. Walter, S. Schinder, L. Rout, and S. M. Huber https://doi.org//10.1055/s-0033-1338981What is Halogen Bond, A Review: Although halogen bonds share many similarities with hydrogen bonds, they have so far found virtually no application in organic synthesis. This account summarizes our efforts to use multidentate halogen-bond donors (halogen-based Lewis acids) in formal halide abstraction reactions. Following a first proof-of-principle study, we recently reported the first halogen-bond-based organocatalytic carbon–carbon bond-forming reaction. |
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17: 5-Iodo-1,2,3-triazolium-based multidentate halogen-bond donors as activating reagents, Chem. Comm,2012, 48, 9299. F. Kniep, L. Rout, S.M. Walter, H. K. V. Bensch, S. H. Jungbauer, E. Herdtweck and S. M. Huber. https://doi.org/10.1039/C2CC34392D
Abstract: Bi- and tridentate polycationic halogen bond donors based on 5-iodo-1,2,3-triazolium groups have been synthesized by 1,3-dipolar cycloaddition reactions. These halogen-based Lewis acids have been evaluated as activators in a halide-abstraction benchmark reaction. |
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16: Isothermal Calorimetric Titrations on Charge-Assisted Halogen Bonds: Role of Entropy, Counterions, Solvent, and Temperature J. Am. Chem. Soc. 2012, 134, 8507-8512. Sebastian M. Walter, Florian Kniep, Laxmidhar Rout, Franz P. Schmidtchen, Eberhardt Herdtweck, Stefan M. Huber. https://doi.org/10.1021/ja2119207
Abstrcat: We have conducted isothermal calorimetric titrations to investigate the halogen-bond strength of cationic bidentate halogen-bond donors toward halides, using bis(iodoimidazolium) compounds as probes. These data are intended to aid the rational design of halogen-bond donors as well as the development of halogen-bond-based applications in solution. In all cases examined, the entropic contribution to the overall free energy of binding was found to be very important. The binding affinities showed little dependency on the weakly coordinating counteranions of the halogen-bond donors but became slightly stronger with higher temperatures. We also found a marked influence of different solvents on the interaction strength. The highest binding constant detected in this study was 3.3 × 106 M–1. |
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15: Synthesis of a-Arylphosphonates Using Copper-Catalyzed a-Arylation and Deacylative a-Arylation of b-Ketophosphonates. Adv. Synth. Catal. 2011, 353, 3340. L. Rout, S. Regati and C. G. Zhao, https://doi.org/10.1002/adsc.201100605
Abstract: Efficient methods for the direct arylation and deacylative arylation of β-ketophosphonates with iodoarenes in presence of a copper(I) or a copper(II) salt as the catalysts have been developed. The corresponding α-arylphosphonates were obtained in high yields. A tentative mechanism for the deacylative arylation reaction was proposed on the basis of the experimental data.
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14: Organocatalytic Highly Enantioselective Synthesis of b-Formyl-a-hydroxyphosphonates; Adv. Synth. Catal. 2011, 353, 1729. S. Perera, V. K. Naganaboina, L.Wang, B. Zhang, Q. Guo, L. Rout and C.-G. Zhao. https://doi.org/10.1002/adsc.201000835
Abstrcat: The cross-aldol reaction between enolizable aldehydes and α-ketophosphonates was achieved for the first time by using 9-amino-9-deoxy-epi-quinine as the catalyst. β-Formyl-α-hydroxyphosphonates were obtained in high to excellent enantioselectivities. The reaction works especially well with acetaldehyde, which is a tough substrate for organocatalyzed cross-aldol reactions. The products were demonstrated to have anticancer activities.
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13: Allene Carboxylates as Dipolarophiles in Rh‐Catalyzed Carbonyl Ylide Cycloadditions. Chem. Eur. J. 2009, 15, 12926. L. Rout and A. M. Harned., https://doi.org/10.1002/chem.200902208
Abstract: Face-to-face: Allene carboxylates can serve as efficient dipolarophiles for Rh-catalyzed carbonyl ylide cycloadditions (see scheme). The endo and exo products arise from cycloaddition on the same face of the allene, but opposite faces of the dipole. This facial selectivity results in the formation of two of the four possible diastereomers. |
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S. Jammi, S. Sakthivel, L. Rout, T. Mukherjee, S. Mandal, R. Mitra, P. Saha and T. Punniyamurthy, https://doi.org/10.1021/jo8024253
Abstract: CuO nanoparticles have been studied for C−N, C−O, and C−S bond formations via cross-coupling reactions of nitrogen, oxygen, and sulfur nucleophiles with aryl halides. Amides, amines, imidazoles, phenols, alcohols and thiols undergo reactions with aryl iodides in the presence of a base such as KOH, Cs2CO3, and K2CO3 at moderate temperature. The procedure is simple, general, ligand-free, and efficient to afford the cross-coupled products in high yield. |
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11: Synthesis, Structure, and Application of Self-Assembled Copper(II) Aqua Complex by H-Bonding for Acceleration of the Nitroaldol Reaction in Water; Chem. Asian. J. 2009, 4, 314. S. Jammi, Md A. Ali, S. Sakthivel, L. Rout, and T. Punniyamurthy . https://doi.org/10.1002/asia.200800339
Abstract: Simple addition: Copper(II) aqua complex 1 can be prepared in a one-pot synthesis and is self-assembled by H-bond interactions. Complex 1 is shown to accelerate the nitroaldol reaction on water, which is a heterogeneous process, requiring no additive or base, and 1 can be recycled without loss of activity. opper(II) aqua complex 1 has been prepared in a one-pot synthesis. The single crystal X-ray analysis showed that the complex is self-assembled through aqua ligands by H-bond interactions and the copper(II) atoms are pentacoordinated with square pyramidal geometry. Complex 1 has been studied for the acceleration of the nitroalodol reaction on water. It is a clean technological process and the catalyst can be recycled without loss of activity. |
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10: Synthesis, Structure and Application of Chiral Copper(II) Polymers for Asymmetric Acylation of Secondary Alcohols. Inorg. Chem. 2008, 12, 5093. S. Jammi, L. Rout, P. Saha, V. K. Akhilagunta, S. Sanyasi and T. Punniyamurthy, https://doi.org/10.1021/ic800228c
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9. Efficient Ligand-Free Nickel-Catalyzed C-S Cross-Coupling of Thiols with Aryl Iodides. Tetrahedron. Lett. 2008, 49,1484. S. Jammi, P. Barua, L. Rout, P. Saha and T. Punniyamurthy, https://doi.org/10.1016/j.tetlet.2007.12.118 Abstract: NiCl2·6H2O efficiently catalyzes the C–S bond formation by the cross-coupling of aryl iodides with thiols in tetrabutylammonium bromide (TBAB) in excellent yield. The reaction functions in air and the NiLn-TBAB can be recovered and recycled without the loss of activity. |
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8: Efficient Copper(I) Catalyzed C-S Cross-Coupling of Thiols with Aryl Halides in Water; Eur. J. Org. Chem. 2008, 640. L. Rout, P. Saha and T. Punniyamurthy, https://doi.org/10.1002/ejoc.200700978 Abstrcat: CuI efficiently catalyzes the C–S cross coupling of thiols with aryl halides in the presence of tetrabutylammonium bromide in water. The reactions with aryl thiols that have electron-withdrawing and -donating substituents are comparable and afford C–S cross-coupling products in high yield. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008) |
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7: Recent Advances in Copper-Catalyzed Oxidation of Organic Compounds. Coord. Chem. Rev.2008, 252, 134. T. Punniyamurthy and L. Rout, https://doi.org/10.1016/j.ccr.2007.04.003 Abstract: The copper-catalyzed oxidation of organic compounds has made considerable progress in the recent years. Molecular oxygen, aqueous hydrogen peroxide, tert-butyl hydroperoxide and peroxyesters have been employed as terminal oxidants for this purpose. The use of polymer and solid-supported catalysts, ionic liquids and fluorous biphase systems (FBS) has been demonstrated to facilitate the recyclability of the catalysts. Efforts have been made for the aqueous oxidation processes employing water-soluble copper complexes. Chiral catalysts have been designed and developed for the enantioselective oxidative coupling of 2-naphthols, Baeyer–Villiger oxidation and Kharasch–Sosnovsky reaction with high enantioselectivity. |
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6: Cadmium(II) Catalyzed C-N Cross-Coupling of Amines with Aryl Iodides. Adv. Synth. Catal. 2008, 350, 395. L. Rout, S. Jammi and T. Punniyamurthy, https://doi.org/10.1002/adsc.200700480
Abstrcat: Cadmium diacetate dihydrate [Cd(OAc)2⋅2 H2O] in combination with ethylene glycol catalyzes efficiently the CN cross-coupling of amines with aryl iodides by a benzyne mechanism. Alkyl, aryl and heterocyclic amines are compatible with this system affording the aminated products in high to excellent yield. |
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5: Efficient CuO Nanoparticle Catalyzed C-S Cross Coupling of Thiols with Iodobenzene; Angew. Chem. Int. Ed. Eng 2007, 46, 5583. L. Rout, T. K. Sen and T. Punniyamurthy, https://doi.org/10.1002/anie.200701282 Abstract: Cheap but good: Readily available CuO nanoparticles are not only less expensive than other catalysts used for the CS cross-coupling of thiols with aryl halides, but they are also effective at a moderate temperature and low concentration. The title reaction proceeds with a variety of alkyl and aryl thiols to give the corresponding sulfides in high yields.
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4: Novel CuO Nanoparticle Catalyzed C-N Cross-Coupling of Amines with Iodobenzene.; Org. Lett. 2007, 9, 3397. L. Rout, S. Jammi and T. Punniyamurthy, https://doi.org/10.1021/ol0713887
Abstrcat: CuO nanoparticles catalyze the C−N cross coupling of amines with iodobenzene in excellent yields. The reaction is simple and efficient and operates under air with ligand free conditions. The catalyst is recyclable without loss of activity. |
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3: Chiral Linear Polymers Bonded Alternatively with Salen and 1,4-Dialkoxy-2,6-diethynylbenzene: Synthesis and Application to Diethylzinc Addition to Aldehydes. Tetrahedron: Asymmetry 2007,17,2016. S. Jammi, L. Rout and T. Punniyamurthy, https://doi.org/10.1016/j.tetasy.2007.09.004 Abstract : The synthesis of chiral polymers 1 bonded alternatively with salen and 1,4-dialkoxy-2,6-diethynylbenzene was accomplished. These polymers are recyclable and catalyze the Et2Zn addition to aldehydes with good enantioselectivity.
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2: Vanadium-Catalyzed Selective Oxidation of Alcohols to Aldehydes and Ketones with t-BuO2H; Adv. Synth. Catal. 2007, 349, 846. L. Rout and T. Punniyamurthy, https://doi.org/10.1002/adsc.200600397 Abstrcat: The oxidation of alcohols to aldehydes and ketones has been described using silica-supported vanadium(iv) oxide (V/SiO2, 1) in the presence of tert-butyl hydroperoxide in tert-butyl alcohol at ambient temperature with quantitative yields. The procedure is simple, efficient and environmentally benign. |
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1: Silica-Supported Vanadium-Catalyzed N-Oxidation of Tertiary Amines with Aq. H2O2. Adv. Synth. Catal. 2005, 347, 1958. L. Rout and T. Punniyamurthy, https://doi.org/10.1002/adsc.200505166 Abstrcat: A recyclable silica supported vanadium 1 catalyzes the oxidation of tertiray amines to the corresponding N-oxides with 30% H2O2 in high yield
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