Efficient Chemoselective Reduction of N -Oxides and Sulfoxides Using a Carbon-Supported Molybdenum-Dioxo Catalyst and Alcohol

Li, Jiaqi; Liu, Shengsi; Lohr, Tracy L.; Marks, Tobin J.

doi:10.1002/cctc.201900436

Efficient Chemoselective Reduction of N -Oxides and Sulfoxides Using a Carbon-Supported Molybdenum-Dioxo Catalyst and Alcohol

Journal Article · Wed May 15 00:00:00 EDT 2019 · ChemCatChem

DOI:https://doi.org/10.1002/cctc.201900436· OSTI ID:1609430

Li, Jiaqi ^[1]; Liu, Shengsi ^[2]; ^[3]; Marks, Tobin J. ^[2]

Department of ChemistryNorthwestern University 2145 Sheridan Road, Evanston Illinois 60208 USA; DOE/OSTI
Department of ChemistryNorthwestern University 2145 Sheridan Road, Evanston Illinois 60208 USA
Department of ChemistryNorthwestern University 2145 Sheridan Road, Evanston Illinois 60208 USA; Current AddressShell Catalysts &, TechnologiesShell Technology Center Houston 3333 Highway 6 South Houston Texas 77082 USA

Not provided.

Research Organization:: Northwestern Univ., Evanston, IL (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

DOE Contract Number:: FG02-03ER15457

OSTI ID:: 1609430

Journal Information:: ChemCatChem, Journal Name: ChemCatChem Journal Issue: 16 Vol. 11; ISSN 1867-3880

Publisher:: ChemPubSoc Europe

Country of Publication:: United States

Language:: English

References (61)

Homogeneous and Heterogeneous Catalysis: Bridging the Gap through Surface Organometallic Chemistry Copéret, Christophe; Chabanas, Mathieu; Petroff Saint-Arroman, Romain Angewandte Chemie International Edition, Vol. 42, Issue 2, p. 156-181 https://doi.org/10.1002/anie.200390072	journal	January 2003
Catalytic reduction of dimethyl sulfoxide and other sulfoxides with bromine - hydrobromic acid system. Aida, Tetsuo; Furukawa, Naomichi; Oae, Shigeru Tetrahedron Letters, Vol. 14, Issue 39 https://doi.org/10.1016/S0040-4039(01)87056-8	journal	January 1973
Pinacol as a New Green Reducing Agent: Molybdenum- Catalyzed Chemoselective Reduction of Sulfoxides and Nitroaromatics García, Nuria; García-García, Patricia; Fernández-Rodríguez, Manuel A. Advanced Synthesis & Catalysis, Vol. 354, Issue 2-3 https://doi.org/10.1002/adsc.201100877	journal	January 2012
Nitrous Oxide as a Hydrogen Acceptor for the Dehydrogenative Coupling of Alcohols Gianetti, Thomas L.; Annen, Samuel P.; Santiso-Quinones, Gustavo Angewandte Chemie International Edition, Vol. 55, Issue 5 https://doi.org/10.1002/anie.201509288	journal	December 2015
Dichlorodioxomolybdenum(VI) Complexes: Useful and Readily Available Catalysts in Organic Synthesis Hernández-Ruiz, Raquel; Sanz, Roberto Synthesis, Vol. 50, Issue 20 https://doi.org/10.1055/s-0037-1610236	journal	September 2018
Efficient synthesis of 2,5-dihydroxymethylfuran and 2,5-dimethylfuran from 5-hydroxymethylfurfural using mineral-derived Cu catalysts as versatile catalysts Zhu, Yifeng; Kong, Xiao; Zheng, Hongyan Catalysis Science & Technology, Vol. 5, Issue 8 https://doi.org/10.1039/C5CY00700C	journal	January 2015
Efficient deoxygenation methodologies catalyzed by oxo-molybdenum and oxo-rhenium complexes Sousa, Sara C. A.; Fernandes, Ana C. Coordination Chemistry Reviews, Vol. 284 https://doi.org/10.1016/j.ccr.2014.09.008	journal	February 2015
Intramolecular catalysis of organic oxidation and reduction reactions: rapid and microscopically reversible thioether-sulfoxide interconversions in dilute acid Doi, Joyce Takahashi; Musker, W. Kenneth Journal of the American Chemical Society, Vol. 103, Issue 5 https://doi.org/10.1021/ja00395a027	journal	March 1981
A Facile and Efficient Iron-Catalyzed Reduction of Sulfoxides to Sulfides Enthaler, Stephan ChemCatChem, Vol. 3, Issue 4 https://doi.org/10.1002/cctc.201000400	journal	January 2011
A Novel Method for the Deoxygenation of Sulfoxides with the PPh ₃ /Br ₂ /CuBr System Bahrami, Kiumars; Khodaei, Mohammad Mehdi; Khedri, Mohammad Chemistry Letters, Vol. 36, Issue 11 https://doi.org/10.1246/cl.2007.1324	journal	November 2007
Iron-Catalyzed Synthesis of Secondary Amines: On the Way to Green Reductive Aminations Stemmler, Tobias; Surkus, Annette-Enrika; Pohl, Marga-Martina ChemSusChem, Vol. 7, Issue 11 https://doi.org/10.1002/cssc.201402413	journal	September 2014
Nickel-Catalyzed Addition of Pyridine-N-oxides across Alkynes Kanyiva, Kyalo Stephen; Nakao, Yoshiaki; Hiyama, Tamejiro Angewandte Chemie International Edition, Vol. 46, Issue 46 https://doi.org/10.1002/anie.200703758	journal	November 2007
A Study of Acetaldehyde Adsorption on Activated Carbons El-Sayed, Yehya; Bandosz, Teresa J. Journal of Colloid and Interface Science, Vol. 242, Issue 1 https://doi.org/10.1006/jcis.2001.7772	journal	October 2001
Reactions of Thiols with Sulfoxides. II. Kinetics and Mechanistic Implications Wallace, Thomas J.; Mahon, John J. Journal of the American Chemical Society, Vol. 86, Issue 19 https://doi.org/10.1021/ja01073a039	journal	October 1964
Methylrhenium trioxide as a catalyst for oxidations with molecular oxygen and for oxygen transfer Zhu, Zuolin; Espenson, James H. Journal of Molecular Catalysis A: Chemical, Vol. 103, Issue 2 https://doi.org/10.1016/1381-1169(95)00120-4	journal	October 1995
A survey of solvent selection guides Prat, Denis; Hayler, John; Wells, Andy Green Chem., Vol. 16, Issue 10 https://doi.org/10.1039/C4GC01149J	journal	January 2014
A noble-metal free Cu-catalyst derived from hydrotalcite for highly efficient hydrogenation of biomass-derived furfural and levulinic acid Yan, Kai; Liao, Jiayou; Wu, Xu RSC Advances, Vol. 3, Issue 12 https://doi.org/10.1039/c3ra22158j	journal	January 2013
Catalytic deoxygenation of pyridine N-oxides with N-fused porphyrin rhenium complexes Toganoh, Motoki; Fujino, Keitaro; Ikeda, Shinya Tetrahedron Letters, Vol. 49, Issue 9 https://doi.org/10.1016/j.tetlet.2007.12.117	journal	February 2008
A practical and chemoselective Mo-catalysed sulfoxide reduction protocol using a 3-mercaptopropyl-functionalized silica gel (MPS) García, Nuria; Fernández-Rodríguez, Manuel A.; García-García, Patricia RSC Advances, Vol. 6, Issue 32 https://doi.org/10.1039/C6RA03106D	journal	January 2016
Selective Deoxygenation of Sulfoxides to Sulfides with Phosphites Catalyzed by Dichlorodioxomolybdenum(VI) Sanz, Roberto; Escribano, Jaime; Aguado, Rafael Synthesis, Vol. 2004, Issue 10 https://doi.org/10.1055/s-2004-829104	journal	June 2004
Chemoselective hydrogenation of nitroarenes and deoxygenation of pyridine N-oxides with H2 catalyzed by MoO2Cl2 Reis, Patrícia M.; Royo, Beatriz Tetrahedron Letters, Vol. 50, Issue 8 https://doi.org/10.1016/j.tetlet.2008.12.038	journal	February 2009
LiBH4(NaBH4)/Me3SiCl, an Unusually Strong and Versatile Reducing Agent Giannis, Athanassios; Sandhoff, Konrad Angewandte Chemie International Edition in English, Vol. 28, Issue 2 https://doi.org/10.1002/anie.198902181	journal	February 1989
N -Bromosuccinimideand Iodine Catalyzed Highly Efficient Deoxygenation ofSulfoxides to Thioethers Using 3-Mercaptopropionic Acid under Mild ReactionConditions Karimi, Babak; Zareyee, Daryoush Synthesis, Issue 12 https://doi.org/10.1055/s-2003-40981	journal	January 2003
Deoxygenation of Sulfoxides to Sulfides with Thionyl Chloride and Triphenylphosphine: Competition with the Pummerer Reaction Jang, Yujin; Kim, Kyoung Tae; Jeon, Heung Bae The Journal of Organic Chemistry, Vol. 78, Issue 12 https://doi.org/10.1021/jo4008157	journal	June 2013
Handbook of Heterogeneous Catalysis No authors listed https://doi.org/10.1002/9783527610044	book	March 2008
Efficient catalytic greenhouse gas-free hydrogen and aldehyde formation from aqueous alcohol solutions Lohr, Tracy L.; Mouat, Aidan R.; Schweitzer, Neil M. Energy & Environmental Science, Vol. 10, Issue 7 https://doi.org/10.1039/C6EE03739A	journal	January 2017
Highly Efficient Gold Nanoparticle Catalyzed Deoxygenation of Amides, Sulfoxides, and Pyridine N-Oxides Mikami, Yusuke; Noujima, Akifumi; Mitsudome, Takato Chemistry - A European Journal, Vol. 17, Issue 6 https://doi.org/10.1002/chem.201003109	journal	January 2011
Chemoselective Hydrogenation of Nitro Compounds with Supported Gold Catalysts Corma, Avelino; Serna, Pedro Science, Vol. 313, Issue 5785, p. 332-334 https://doi.org/10.1126/science.1128383	journal	July 2006
Efficient Synthesis of Furfuryl Alcohol from H ₂ -Hydrogenation/Transfer Hydrogenation of Furfural Using Sulfonate Group Modified Cu Catalyst Gong, Wanbing; Chen, Chun; Zhang, Yong ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 3 https://doi.org/10.1021/acssuschemeng.6b02343	journal	February 2017
An unprecedented use for glycerol: chemoselective reducing agent for sulfoxides García, Nuria; García-García, Patricia; Fernández-Rodríguez, Manuel A. Green Chemistry, Vol. 15, Issue 4 https://doi.org/10.1039/c3gc36908k	journal	January 2013
Molybdenum-Catalyzed Deoxygenation of Heteroaromatic N- Oxides and Hydroxides using Pinacol as Reducing Agent Rubio-Presa, Rubén; Fernández-Rodríguez, Manuel A.; Pedrosa, María R. Advanced Synthesis & Catalysis, Vol. 359, Issue 10 https://doi.org/10.1002/adsc.201700071	journal	March 2017
Reduction of sulfoxides with boranes catalyzed by MoO2Cl2 Fernandes, Ana C.; Romão, Carlos C. Tetrahedron Letters, Vol. 48, Issue 52 https://doi.org/10.1016/j.tetlet.2007.10.106	journal	December 2007
Pyridine N -Oxide vs Pyridine Substrates for Rh(III)-Catalyzed Oxidative C–H Bond Functionalization Neufeldt, Sharon R.; Jiménez-Osés, Gonzalo; Huckins, John R. Journal of the American Chemical Society, Vol. 137, Issue 31 https://doi.org/10.1021/jacs.5b03535	journal	July 2015
A gentle and efficient route for the deoxygenation of sulfoxides using catecholborane (HBcat; cat=1,2-O2C6H4) Harrison, Daniel J.; Tam, Nga Chiu; Vogels, Christopher M. Tetrahedron Letters, Vol. 45, Issue 46 https://doi.org/10.1016/j.tetlet.2004.09.068	journal	November 2004
The deoxygenation of sulfoxide mediated by the Ph3P/Lewis acid combination and the application to the kinetic resolution of racemic phosphines using optically active sulfoxide Kikuchi, Satoshi; Konishi, Hiroyuki; Hashimoto, Yukihiko Tetrahedron, Vol. 61, Issue 14 https://doi.org/10.1016/j.tet.2005.01.127	journal	April 2005
Definition of green synthetic tools based on safer reaction media, heterogeneous catalysis, and flow technology Vaccaro, Luigi; Curini, Massimo; Ferlin, Francesco Pure and Applied Chemistry, Vol. 90, Issue 1 https://doi.org/10.1515/pac-2017-0409	journal	January 2018
Hydrogen activation by high-valent oxo-molybdenum(vi) and -rhenium(vii) and -(v) compounds Reis, Patrícia M.; Costa, Paulo Jorge; Romão, Carlos C. Dalton Transactions, Issue 13 https://doi.org/10.1039/b719375k	journal	January 2008
Nickel-Catalyzed Addition of Pyridine-N-oxides across Alkynes Kanyiva, Kyalo Stephen; Nakao, Yoshiaki; Hiyama, Tamejiro Angewandte Chemie, Vol. 119, Issue 46 https://doi.org/10.1002/ange.200703758	journal	November 2007
Rhenium catalyzed sulfoxide reduction Arterburn, Jeffrey B.; Perry, Marc C. Tetrahedron Letters, Vol. 37, Issue 44 https://doi.org/10.1016/0040-4039(96)01836-9	journal	October 1996
Reactivity of a Carbon-Supported Single-Site Molybdenum Dioxo Catalyst for Biodiesel Synthesis Mouat, Aidan R.; Lohr, Tracy L.; Wegener, Evan C. ACS Catalysis, Vol. 6, Issue 10 https://doi.org/10.1021/acscatal.6b01717	journal	September 2016
Recent Advances in Catalytic Functionalization of N -Oxide Compounds via CH Bond Activation Yan, Guobing; Borah, Arun Jyoti; Yang, Minghua Advanced Synthesis & Catalysis, Vol. 356, Issue 11-12 https://doi.org/10.1002/adsc.201400203	journal	June 2014
Homogene und heterogene Katalyse – Brückenschlag durch Oberflächen-Organometallchemie Copéret, Christophe; Chabanas, Mathieu; Petroff Saint-Arroman, Romain Angewandte Chemie, Vol. 115, Issue 2 https://doi.org/10.1002/ange.200390040	journal	January 2003
Mild and Efficient Deoxygenation of Sulfoxides to Sulfides Using HfCl ₄ /KBH ₄ System Zhang, Jianghua; Gao, Xinqin; Zhang, Chengyi Synthetic Communications, Vol. 40, Issue 12 https://doi.org/10.1080/00397910903161819	journal	May 2010
LiBH4(NaBH4)/Me3SiCl, ein ungewöhnlich starkes und vielseitig einsetzbares Reduktionsmittel Giannis, Athanassios; Sandhoff, Konrad Angewandte Chemie, Vol. 101, Issue 2 https://doi.org/10.1002/ange.19891010231	journal	February 1989
Low‐Valent Molybdenum‐Based Dual Pre‐Catalysts for Highly Efficient Catalytic Epoxidation of Alkenes and Deoxygenation of Sulfoxides Krackl, Sebastian; Company, Anna; Enthaler, Stephan ChemCatChem, Vol. 3, Issue 7 https://doi.org/10.1002/cctc.201100007	journal	April 2011
Racemization of sulphoxides with halide ions anchimerically assisted by a carboxy-group. The different behaviour of chloride and bromide ions Landini, Dario; Maia, Angela Maria; Rolla, Franco Journal of the Chemical Society, Perkin Transactions 2, Issue 12 https://doi.org/10.1039/p29760001288	journal	January 1976
Furfural: a renewable and versatile platform molecule for the synthesis of chemicals and fuels Mariscal, R.; Maireles-Torres, P.; Ojeda, M. Energy & Environmental Science, Vol. 9, Issue 4 https://doi.org/10.1039/C5EE02666K	journal	January 2016
Efficient carbon-supported heterogeneous molybdenum-dioxo catalyst for chemoselective reductive carbonyl coupling Liu, Shengsi; Li, Jiaqi; Jurca, Titel Catalysis Science & Technology, Vol. 7, Issue 11 https://doi.org/10.1039/C7CY00336F	journal	January 2017
Hydrogenation of Sulfoxides to Sulfides under Mild Conditions Using Ruthenium Nanoparticle Catalysts Mitsudome, Takato; Takahashi, Yusuke; Mizugaki, Tomoo Angewandte Chemie, Vol. 126, Issue 32 https://doi.org/10.1002/ange.201403425	journal	June 2014
Reduction of sulfoxides and pyridine-N-oxides over iron powder with water as hydrogen source promoted by carbon dioxide Ma, Ran; Liu, An-Hua; Huang, Cheng-Bin Green Chemistry, Vol. 15, Issue 5 https://doi.org/10.1039/c3gc40243f	journal	January 2013
Efficient Synthesis of Furfuryl Alcohol and 2-Methylfuran from Furfural over Mineral-Derived Cu/ZnO Catalysts Yang, Xiaohai; Xiang, Xiaomin; Chen, Hongmei ChemCatChem, Vol. 9, Issue 15 https://doi.org/10.1002/cctc.201700279	journal	June 2017
Highly Efficient Reduction of Sulfoxides with the System Borane/Oxo-rhenium Complexes ^† Fernandes, Ana C.; Fernandes, José A.; Romão, Carlos C. Organometallics, Vol. 29, Issue 21 https://doi.org/10.1021/om100450a	journal	November 2010
CHEM21 selection guide of classical- and less classical-solvents Prat, Denis; Wells, Andy; Hayler, John Green Chemistry, Vol. 18, Issue 1 https://doi.org/10.1039/C5GC01008J	journal	January 2016
Catalytic Deoxygenation of Sulfoxides by Molecular Hydrogen and its Application to the Homologation of Aromatic Aldehydes Ogura, K.; Yamashita, M.; Tsuchihashi, G. Synthesis, Vol. 1975, Issue 06 https://doi.org/10.1055/s-1975-23763	journal	January 1975
XLV.—Benzyl sulphoxide: a possible example of dynamic isomerism Smythe, John Armstrong J. Chem. Soc., Trans., Vol. 95, Issue 0 https://doi.org/10.1039/ct9099500349	journal	January 1909
Reduction of sulfoxides catalyzed by oxo-complexes Cabrita, Ivânia; Sousa, Sara C. A.; Fernandes, Ana C. Tetrahedron Letters, Vol. 51, Issue 47 https://doi.org/10.1016/j.tetlet.2010.09.071	journal	November 2010
A novel method for the reduction of sulfoxides and pyridine N-oxides with the system silane/MoO2Cl2 Fernandes, Ana C.; Romão, Carlos C. Tetrahedron, Vol. 62, Issue 41 https://doi.org/10.1016/j.tet.2006.07.077	journal	October 2006
Hydrogenation of Sulfoxides to Sulfides under Mild Conditions Using Ruthenium Nanoparticle Catalysts Mitsudome, Takato; Takahashi, Yusuke; Mizugaki, Tomoo Angewandte Chemie International Edition, Vol. 53, Issue 32 https://doi.org/10.1002/anie.201403425	journal	June 2014
Nitrous Oxide as a Hydrogen Acceptor for the Dehydrogenative Coupling of Alcohols Gianetti, Thomas L.; Annen, Samuel P.; Santiso-Quinones, Gustavo Angewandte Chemie, Vol. 128, Issue 5 https://doi.org/10.1002/ange.201509288	journal	December 2015
Catalytic 1,2-Regioselective Dearomatization of N-Heteroaromatics via a Hydroboration Liu, Heng; Khononov, Maxim; Eisen, Moris S. ACS Catalysis, Vol. 8, Issue 4 https://doi.org/10.1021/acscatal.8b00074	journal	March 2018
Biorefining: Heterogeneously Catalyzed Reactions of Carbohydrates for the Production of Furfural and Hydroxymethylfurfural Karinen, Reetta; Vilonen, Kati; Niemelä, Marita ChemSusChem, Vol. 4, Issue 8 https://doi.org/10.1002/cssc.201000375	journal	July 2011

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