Selective Synthesis of 4,'-Dimethylbiphenyl from 2-Methylfuran

Cho, Hong Je; Kuo, Mi Jen; Ye, Mingchun; Kurz, Yannick; Yuan, Yong; Lobo, Raul F.

doi:10.1021/acssuschemeng.0c09227

Selective Synthesis of 4,'-Dimethylbiphenyl from 2-Methylfuran

Journal Article · Tue Feb 16 23:00:00 EST 2021 · ACS Sustainable Chemistry & Engineering

DOI:https://doi.org/10.1021/acssuschemeng.0c09227· OSTI ID:1850656

^[1]; Kuo, Mi Jen ^[2]; ^[2]; Kurz, Yannick ^[3]; Yuan, Yong ^[2]; ^[2]

Catalysis Center for Energy Innovation, Department of Chemical and Biomolecular Engineering, University of Delaware, Newark, Delaware 19716, United States; OSTI
Catalysis Center for Energy Innovation, Department of Chemical and Biomolecular Engineering, University of Delaware, Newark, Delaware 19716, United States
Catalysis Center for Energy Innovation, Department of Chemical and Biomolecular Engineering, University of Delaware, Newark, Delaware 19716, United States; Department of Chemistry and Applied Biosciences, ETH Zürich, Vladimir-Prelog-Weg 1-5/10, 8093 Zürich, Switzerland

Not provided.

Research Organization:: Univ. of Delaware, Newark, DE (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

DOE Contract Number:: SC0001004

OSTI ID:: 1850656

Journal Information:: ACS Sustainable Chemistry & Engineering, Journal Name: ACS Sustainable Chemistry & Engineering Journal Issue: 8 Vol. 9; ISSN 2168-0485

Publisher:: American Chemical Society (ACS)

Country of Publication:: United States

Language:: English

References (52)

Mechanistic Insights into Metal Lewis Acid-Mediated Catalytic Transfer Hydrogenation of Furfural to 2-Methylfuran Gilkey, Matthew J.; Panagiotopoulou, Paraskevi; Mironenko, Alexander V. ACS Catalysis, Vol. 5, Issue 7 https://doi.org/10.1021/acscatal.5b00586	journal	June 2015
Four MOFs with 2,2′-dimethoxy-4,4′-biphenyldicarboxylic acid: syntheses, structures, topologies and properties Luo, Rui; Xu, Heng; Gu, Hao-Xue CrystEngComm, Vol. 16, Issue 5 https://doi.org/10.1039/C3CE41428K	journal	January 2014
Synthesis and characterization of a fire-retardant polyester: Copolymers of ethylene terephthalate and 2-carboxyethyl(phenylphosphinic) acid Asrar, Jawed; Berger, Pierre A.; Hurlbut, Jeffrey Journal of Polymer Science Part A: Polymer Chemistry, Vol. 37, Issue 16 https://doi.org/10.1002/(SICI)1099-0518(19990815)37:16<3119::AID-POLA9>3.0.CO;2-7	journal	August 1999
Integrating Biomass into the Organonitrogen Chemical Supply Chain: Production of Pyrrole and d ‐Proline from Furfural Song, Song; Fung Kin Yuen, Vincent; Di, Lu Angewandte Chemie International Edition, Vol. 59, Issue 45 https://doi.org/10.1002/anie.202006315	journal	August 2020
Pd(OAc)2 catalyzed homocoupling of arenediazonium salts in ionic liquids: synthesis of symmetrical biaryls Savanur, Hemantkumar M.; Kalkhambkar, Rajesh G.; Laali, Kenneth K. Tetrahedron Letters, Vol. 57, Issue 6 https://doi.org/10.1016/j.tetlet.2015.12.108	journal	February 2016
Alternative Monomers Based on Lignocellulose and Their Use for Polymer Production Delidovich, Irina; Hausoul, Peter J. C.; Deng, Li Chemical Reviews, Vol. 116, Issue 3 https://doi.org/10.1021/acs.chemrev.5b00354	journal	November 2015
Catalytic synthesis of renewable p-xylene from biomass-derived 2,5-dimethylfuran: a mini review Dutta, Saikat; Bhat, Navya Subray Biomass Conversion and Biorefinery https://doi.org/10.1007/s13399-020-01042-z	journal	October 2020
Biomass-Derived Butadiene by Dehydra-Decyclization of Tetrahydrofuran Abdelrahman, Omar A.; Park, Dae Sung; Vinter, Katherine P. ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 5 https://doi.org/10.1021/acssuschemeng.7b00745	journal	March 2017
Synthesis of Cyclic Enones via Direct Palladium-Catalyzed Aerobic Dehydrogenation of Ketones Diao, Tianning; Stahl, Shannon S. Journal of the American Chemical Society, Vol. 133, Issue 37 https://doi.org/10.1021/ja206575j	journal	August 2011
Palladium‐Catalyzed Oxidative Carbocyclization–Carbonylation of Allenynes and Enallenes Volla, Chandra M. R.; Mazuela, Javier; Bäckvall, Jan‐E. Chemistry – A European Journal, Vol. 20, Issue 25 https://doi.org/10.1002/chem.201402688	journal	May 2014
Generation of Brønsted acid sites on Si-MCM-41 by grafting of phosphorus species Kawi, S.; Shen, S. C.; Chew, P. L. Journal of Materials Chemistry, Vol. 12, Issue 5 https://doi.org/10.1039/b107795n	journal	March 2002
Structure and bonding in metal sulfoxide complexes: an update Calligaris, Mario Coordination Chemistry Reviews, Vol. 248, Issue 3-4 https://doi.org/10.1016/j.ccr.2004.02.005	journal	February 2004
Aerobic Dehydrogenation of Cyclohexanone to Cyclohexenone Catalyzed by Pd(DMSO) ₂ (TFA) ₂ : Evidence for Ligand-Controlled Chemoselectivity Diao, Tianning; Pun, Doris; Stahl, Shannon S. Journal of the American Chemical Society, Vol. 135, Issue 22 https://doi.org/10.1021/ja4031648	journal	May 2013
Renewable Isoprene by Sequential Hydrogenation of Itaconic Acid and Dehydra-Decyclization of 3-Methyl-Tetrahydrofuran Abdelrahman, Omar A.; Park, Dae Sung; Vinter, Katherine P. ACS Catalysis, Vol. 7, Issue 2 https://doi.org/10.1021/acscatal.6b03335	journal	January 2017
Lignocellulosic biomass: a sustainable platform for the production of bio-based chemicals and polymers Isikgor, Furkan H.; Becer, C. Remzi Polymer Chemistry, Vol. 6, Issue 25 https://doi.org/10.1039/C5PY00263J	journal	January 2015
Ethylene hydration over metal phosphates impregnated with phosphoric acid Fougret, C. M.; Hölderich, W. F. Applied Catalysis A: General, Vol. 207, Issue 1-2 https://doi.org/10.1016/S0926-860X(00)00666-9	journal	February 2001
Advances in porous and nanoscale catalysts for viable biomass conversion Sudarsanam, Putla; Peeters, Elise; Makshina, Ekaterina V. Chemical Society Reviews, Vol. 48, Issue 8 https://doi.org/10.1039/C8CS00452H	journal	January 2019
Modular Synthesis of 1,2-Diamine Derivatives by Palladium-Catalyzed Aerobic Oxidative Cyclization of Allylic Sulfamides McDonald, Richard I.; Stahl, Shannon S. Angewandte Chemie, Vol. 122, Issue 32 https://doi.org/10.1002/ange.200906342	journal	June 2010
Renewability is not Enough: Recent Advances in the Sustainable Synthesis of Biomass-Derived Monomers and Polymers Llevot, Audrey; Dannecker, Patrick-Kurt; von Czapiewski, Marc Chemistry - A European Journal, Vol. 22, Issue 33 https://doi.org/10.1002/chem.201602068	journal	June 2016
Selectivity Control in Tandem Catalytic Furfural Upgrading on Zeolite-Encapsulated Pt Nanoparticles through Site and Solvent Engineering Cho, Hong Je; Kim, Doyoung; Xu, Bingjun ACS Catalysis, Vol. 10, Issue 8 https://doi.org/10.1021/acscatal.0c00472	journal	March 2020
Dehydration of Ethanol to Ethylene Zhang, Minhua; Yu, Yingzhe Industrial & Engineering Chemistry Research, Vol. 52, Issue 28 https://doi.org/10.1021/ie401157c	journal	July 2013
Palladium(II)-catalyzed carboxylation of benzene and other aromatic compounds with carbon monoxide under very mild conditions Lu, Wenjun; Yamaoka, Yoshinori; Taniguchi, Yuki Journal of Organometallic Chemistry, Vol. 580, Issue 2 https://doi.org/10.1016/S0022-328X(98)01160-7	journal	May 1999
Characterization of DMSO Coordination to Palladium(II) in Solution and Insights into the Aerobic Oxidation Catalyst, Pd(DMSO) ₂ (TFA) ₂ Diao, Tianning; White, Paul; Guzei, Ilia Inorganic Chemistry, Vol. 51, Issue 21 https://doi.org/10.1021/ic301799p	journal	October 2012
Acylation of methylfuran with Brønsted and Lewis acid zeolites Koehle, Maura; Zhang, Zhiqiang; Goulas, Konstantinos A. Applied Catalysis A: General, Vol. 564 https://doi.org/10.1016/j.apcata.2018.06.005	journal	August 2018
Selectivity Control in Photocatalytic Valorization of Biomass-Derived Platform Compounds by Surface Engineering of Titanium Oxide Wu, Xuejiao; Li, Jieqiong; Xie, Shunji Chem, Vol. 6, Issue 11 https://doi.org/10.1016/j.chempr.2020.08.014	journal	November 2020
Pd-Catalyzed Aerobic Oxidative Coupling of Arenes: Evidence for Transmetalation between Two Pd(II)-Aryl Intermediates Wang, Dian; Izawa, Yusuke; Stahl, Shannon S. Journal of the American Chemical Society, Vol. 136, Issue 28 https://doi.org/10.1021/ja505405u	journal	June 2014
Ligand-Promoted Palladium-Catalyzed Aerobic Oxidation Reactions Wang, Dian; Weinstein, Adam B.; White, Paul B. Chemical Reviews, Vol. 118, Issue 5 https://doi.org/10.1021/acs.chemrev.7b00334	journal	October 2017
Twofold C−H Functionalization: Palladium-Catalyzed Ortho Arylation of Anilides Brasche, Gordon; García-Fortanet,, Jorge; Buchwald, Stephen L. Organic Letters, Vol. 10, Issue 11 https://doi.org/10.1021/ol800619c	journal	June 2008
Renewable p -Xylene from 2,5-Dimethylfuran and Ethylene Using Phosphorus-Containing Zeolite Catalysts Cho, Hong Je; Ren, Limin; Vattipalli, Vivek ChemCatChem, Vol. 9, Issue 3 https://doi.org/10.1002/cctc.201601294	journal	January 2017
Renewable lubricants with tailored molecular architecture Liu, Sibao; Josephson, Tyler R.; Athaley, Abhay Science Advances, Vol. 5, Issue 2 https://doi.org/10.1126/sciadv.aav5487	journal	February 2019
Palladium-Catalyzed C–H Homocoupling of Furans and Thiophenes Using Oxygen as the Oxidant Li, Na-Na; Zhang, Yan-Lei; Mao, Shuai Organic Letters, Vol. 16, Issue 10 https://doi.org/10.1021/ol501019y	journal	May 2014
Intramolecular Pd(II)-Catalyzed Aerobic Oxidative Amination of Alkenes: Synthesis of Six-Membered N -Heterocycles Lu, Zhan; Stahl, Shannon S. Organic Letters, Vol. 14, Issue 5 https://doi.org/10.1021/ol300030w	journal	February 2012
Molecular-Level Proximity of Metal and Acid Sites in Zeolite-Encapsulated Pt Nanoparticles for Selective Multistep Tandem Catalysis Cho, Hong Je; Kim, Doyoung; Li, Shuang ACS Catalysis, Vol. 10, Issue 5 https://doi.org/10.1021/acscatal.9b03842	journal	December 2019
Determination of Integrated Molar Extinction Coefficients for Infrared Absorption Bands of Pyridine Adsorbed on Solid Acid Catalysts Emeis, C. A. Journal of Catalysis, Vol. 141, Issue 2 https://doi.org/10.1006/JCAT.1993.1145	journal	June 1993
Xylose Isomerization to Xylulose and its Dehydration to Furfural in Aqueous Media Choudhary, Vinit; Pinar, Ana B.; Sandler, Stanley I. ACS Catalysis, Vol. 1, Issue 12 https://doi.org/10.1021/cs200461t	journal	October 2011
Complete Field Guide to Asymmetric BINOL-Phosphate Derived Brønsted Acid and Metal Catalysis: History and Classification by Mode of Activation; Brønsted Acidity, Hydrogen Bonding, Ion Pairing, and Metal Phosphates Parmar, Dixit; Sugiono, Erli; Raja, Sadiya Chemical Reviews, Vol. 114, Issue 18 https://doi.org/10.1021/cr5001496	journal	September 2014
Phosphoric acid on oxide carriers. 1. Characterization of silica, alumina, and titania impregnated by phosphoric acid Busca, Guido; Ramis, Gianguido; Lorenzelli, Vincenzo Langmuir, Vol. 5, Issue 4 https://doi.org/10.1021/la00088a005	journal	July 1989
Palladium-Catalyzed Stereoselective Intramolecular Oxidative Amidation of Alkenes in the Synthesis of 1,3- and 1,4-Amino Alcohols and 1,3-Diamines Malkov, Andrei V.; Lee, Darren S.; Barłóg, Maciej Chemistry - A European Journal, Vol. 20, Issue 17 https://doi.org/10.1002/chem.201400123	journal	March 2014
Tuning of nanostructured SBA-15 silica using phosphoric acid Pitchumani, Raghuraman; Li, Wenjiang; Coppens, Marc-Olivier Catalysis Today, Vol. 105, Issue 3-4 https://doi.org/10.1016/j.cattod.2005.06.002	journal	August 2005
Three Novel Metal-Organic Frameworks with Different Topologies Based on 3,3′-Dimethoxy-4,4′-biphenyldicarboxylic Acid: Syntheses, Structures, and Properties Wang, Xiao-Zhu; Zhu, Dun-Ru; Xu, Yan Crystal Growth & Design, Vol. 10, Issue 2 https://doi.org/10.1021/cg9012262	journal	December 2009
Bioethanol production from renewable sources: Current perspectives and technological progress Zabed, H.; Sahu, J. N.; Suely, A. Renewable and Sustainable Energy Reviews, Vol. 71 https://doi.org/10.1016/j.rser.2016.12.076	journal	May 2017
Arylation of non-activated C–Cl bond with Grignard reagents catalyzed by pincer [PCP]-nickel complexes Sun, Yunqiang; Li, Xiaoyan; Sun, Hongjian Inorganica Chimica Acta, Vol. 415 https://doi.org/10.1016/j.ica.2014.02.030	journal	May 2014
Structure and bonding in metal sulfoxide complexes Calligaris, M. Coordination Chemistry Reviews, Vol. 153 https://doi.org/10.1016/0010-8545(95)01193-5	journal	August 1996
Production of High-Quality Diesel from Biomass Waste Products Corma, Avelino; de la Torre, Olalla; Renz, Michael Angewandte Chemie International Edition, Vol. 50, Issue 10 https://doi.org/10.1002/anie.201007508	journal	January 2011
Effect of liquid water on acid sites of NaY: An in situ liquid phase spectroscopic study Gould, Nicholas S.; Xu, Bingjun Journal of Catalysis, Vol. 342 https://doi.org/10.1016/j.jcat.2016.08.008	journal	October 2016
Shape-selective C–H activation of aromatics to biarylic compounds using molecular palladium in zeolites Vercammen, Jannick; Bocus, Massimo; Neale, Sam Nature Catalysis, Vol. 3, Issue 12 https://doi.org/10.1038/s41929-020-00533-6	journal	November 2020
Diels–Alder cycloaddition of 2-methylfuran and ethylene for renewable toluene Green, Sara K.; Patet, Ryan E.; Nikbin, Nima Applied Catalysis B: Environmental, Vol. 180 https://doi.org/10.1016/j.apcatb.2015.06.044	journal	January 2016
A New Porous MOF with Two Uncommon Metal–Carboxylate–Pyrazolate Clusters and High CO ₂ /N ₂ Selectivity Wang, Hai-Hua; Jia, Li-Na; Hou, Lei Inorganic Chemistry, Vol. 54, Issue 4 https://doi.org/10.1021/ic502733v	journal	January 2015
Aerobic Dehydrogenation of Cyclohexanone to Phenol Catalyzed by Pd(TFA) ₂ /2-Dimethylaminopyridine: Evidence for the Role of Pd Nanoparticles Pun, Doris; Diao, Tianning; Stahl, Shannon S. Journal of the American Chemical Society, Vol. 135, Issue 22 https://doi.org/10.1021/ja403165u	journal	May 2013
Calculation of Flame Ionization Detector Relative Response Factors Using the Effective Carbon Number Concept Scanlon, J. T.; Willis, D. E. Journal of Chromatographic Science, Vol. 23, Issue 8 https://doi.org/10.1093/chromsci/23.8.333	journal	August 1985
CCDC 1987601: Experimental Crystal Structure Determination Yannick, Kurz,; F., Lobo, Raul; A., Yap, Glenn P. Cambridge Crystallographic Data Centre https://doi.org/10.5517/ccdc.csd.cc24q85b	dataset	January 2020
On the oligomerization mechanism of Brønsted acid-catalyzed conversion of furans to diesel-range fuels Nikbin, Nima; Caratzoulas, Stavros; Vlachos, Dionisios G. Applied Catalysis A: General, Vol. 485 https://doi.org/10.1016/j.apcata.2014.07.035	journal	September 2014

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