MOF-253-Pd(OAc)2 : a recyclable MOF for transition-metal catalysis in water

Van Zeeland, Ryan; Li, Xinle; Huang, Wenyu; Stanley, Levi M.

doi:10.1039/c6ra12746k

MOF-253-Pd(OAc)₂ : a recyclable MOF for transition-metal catalysis in water

Journal Article · Mon Jun 06 00:00:00 EDT 2016 · RSC Advances

DOI:https://doi.org/10.1039/c6ra12746k· OSTI ID:1326831

Van Zeeland, Ryan ^[1]; Li, Xinle ^[2]; Huang, Wenyu ^[2]; Stanley, Levi M. ^[1]

Iowa State Univ., Ames, IA (United States). Dept. of Chemistry
Iowa State Univ., Ames, IA (United States). Dept. of Chemistry; Ames Lab., Ames, IA (United States)

We report palladium(II)-functionalized MOF-253 (MOF-253-Pd(OAc)₂) as a recyclable catalyst to form all-carbon quaternary centers via conjugate additions of arylboronic acids to β,β-disubstituted enones in aqueous media. We demonstrate MOF-253-Pd(OAc)₂ can be reused 8 times to form ketone products in yields above 75% while maintaining its crystallinity. Additions of a range of stereoelectronically diverse arylboronic acids to a variety of β,β-disubstituted enones catalyzed by MOF-253-Pd(OAc)₂ occur in modest-to-high yields (34–95%).

View Accepted Manuscript (DOE)

Research Organization:: Ames Laboratory (AMES), Ames, IA (United States)

Sponsoring Organization:: USDOE

Grant/Contract Number:: AC02-07CH11358

OSTI ID:: 1326831

Report Number(s):: IS-J--9053

Journal Information:: RSC Advances, Journal Name: RSC Advances Journal Issue: 61 Vol. 6; ISSN 2046-2069; ISSN RSCACL

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

References (46)

Ruthenium Complexation in an Aluminium Metal-Organic Framework and Its Application in Alcohol Oxidation Catalysis Carson, Fabian; Agrawal, Santosh; Gustafsson, Mikaela Chemistry - A European Journal, Vol. 18, Issue 48 https://doi.org/10.1002/chem.201200885	journal	October 2012
Solventless Oxidative Coupling of Amines to Imines by Using Transition-Metal-Free Metal-Organic Frameworks Qiu, Xuan; Len, Christophe; Luque, Rafael ChemSusChem, Vol. 7, Issue 6 https://doi.org/10.1002/cssc.201301340	journal	May 2014
The Slow-Release Strategy in Suzuki-Miyaura Coupling Lennox, Alastair J. J.; Lloyd-Jones, Guy C. Israel Journal of Chemistry, Vol. 50, Issue 5-6 https://doi.org/10.1002/ijch.201000074	journal	December 2010
Heterogeneous heck coupling in multivariate metal–organic frameworks for enhanced selectivity Brown, Jonathan W.; Jarenwattananon, Nanette N.; Otto, Trenton Catalysis Communications, Vol. 65 https://doi.org/10.1016/j.catcom.2015.03.005	journal	May 2015
Immobilization of Pd(II) on MOFs as a highly active heterogeneous catalyst for Suzuki–Miyaura and Ullmann-type coupling reactions Chen, Liyu; Gao, Zhiqiang; Li, Yingwei Catalysis Today, Vol. 245 https://doi.org/10.1016/j.cattod.2014.03.074	journal	May 2015
Counteranion effects on the catalytic activity of copper salts immobilized on the 2,2′-bipyridine-functionalized metal–organic framework MOF-253 Valvekens, Pieterjan; Bloch, Eric D.; Long, Jeffrey R. Catalysis Today, Vol. 246 https://doi.org/10.1016/j.cattod.2014.08.006	journal	May 2015
Palladium-Catalyzed Conjugate Addition of Arylboronic Acids to β,β-Disubstituted Enones in Aqueous Media: Formation of Bis-benzylic and ortho -Substituted Benzylic Quaternary Centers Van Zeeland, Ryan; Stanley, Levi M. ACS Catalysis, Vol. 5, Issue 9 https://doi.org/10.1021/acscatal.5b01272	journal	August 2015
Gas-Phase Dimerization of Ethylene under Mild Conditions Catalyzed by MOF Materials Containing (bpy)Ni ^II Complexes Madrahimov, Sherzod T.; Gallagher, James R.; Zhang, Guanghui ACS Catalysis, Vol. 5, Issue 11 https://doi.org/10.1021/acscatal.5b01604	journal	October 2015
Organic Reactions in Aqueous Media with a Focus on Carbon−Carbon Bond Formations: A Decade Update Li, Chao-Jun Chemical Reviews, Vol. 105, Issue 8 https://doi.org/10.1021/cr030009u	journal	August 2005
Ligand Effects in Homogeneous Au Catalysis Gorin, David J.; Sherry, Benjamin D.; Toste, F. Dean Chemical Reviews, Vol. 108, Issue 8 https://doi.org/10.1021/cr068430g	journal	August 2008
Homochiral Metal–Organic Frameworks for Asymmetric Heterogeneous Catalysis Yoon, Minyoung; Srirambalaji, Renganathan; Kim, Kimoon Chemical Reviews, Vol. 112, Issue 2, p. 1196-1231 https://doi.org/10.1021/cr2003147	journal	September 2011
Dehydrogenation as a Substrate-Activating Strategy in Homogeneous Transition-Metal Catalysis Dobereiner, Graham E.; Crabtree, Robert H. Chemical Reviews, Vol. 110, Issue 2 https://doi.org/10.1021/cr900202j	journal	February 2010
Doping Metal–Organic Frameworks for Water Oxidation, Carbon Dioxide Reduction, and Organic Photocatalysis Wang, Cheng; Xie, Zhigang; deKrafft, Kathryn E. Journal of the American Chemical Society, Vol. 133, Issue 34, p. 13445-13454 https://doi.org/10.1021/ja203564w	journal	August 2011
Elucidating Molecular Iridium Water Oxidation Catalysts Using Metal–Organic Frameworks: A Comprehensive Structural, Catalytic, Spectroscopic, and Kinetic Study Wang, Cheng; Wang, Jin-Liang; Lin, Wenbin Journal of the American Chemical Society, Vol. 134, Issue 48 https://doi.org/10.1021/ja310074j	journal	November 2012
Postsynthetic Metalation of Bipyridyl-Containing Metal–Organic Frameworks for Highly Efficient Catalytic Organic Transformations Manna, Kuntal; Zhang, Teng; Lin, Wenbin Journal of the American Chemical Society, Vol. 136, Issue 18 https://doi.org/10.1021/ja5018267	journal	April 2014
Turning On Catalysis: Incorporation of a Hydrogen-Bond-Donating Squaramide Moiety into a Zr Metal–Organic Framework McGuirk, C. Michael; Katz, Michael J.; Stern, Charlotte L. Journal of the American Chemical Society, Vol. 137, Issue 2 https://doi.org/10.1021/ja511403t	journal	January 2015
Bipyridine- and Phenanthroline-Based Metal–Organic Frameworks for Highly Efficient and Tandem Catalytic Organic Transformations via Directed C–H Activation Manna, Kuntal; Zhang, Teng; Greene, Francis X. Journal of the American Chemical Society, Vol. 137, Issue 7 https://doi.org/10.1021/ja512478y	journal	February 2015
Improved Catalytic Activity and Stability of a Palladium Pincer Complex by Incorporation into a Metal–Organic Framework Burgess, Samantha A.; Kassie, Abebu; Baranowski, Sarah A. Journal of the American Chemical Society, Vol. 138, Issue 6 https://doi.org/10.1021/jacs.5b12366	journal	February 2016
Metal–Organic Frameworks Stabilize Solution-Inaccessible Cobalt Catalysts for Highly Efficient Broad-Scope Organic Transformations Zhang, Teng; Manna, Kuntal; Lin, Wenbin Journal of the American Chemical Society, Vol. 138, Issue 9 https://doi.org/10.1021/jacs.6b00849	journal	February 2016
Immobilization of Cu Complex into Zr-Based MOF with Bipyridine Units for Heterogeneous Selective Oxidation Toyao, Takashi; Miyahara, Kenta; Fujiwaki, Mika The Journal of Physical Chemistry C, Vol. 119, Issue 15 https://doi.org/10.1021/jp512749y	journal	April 2015
Anchoring of Palladium onto Surface of Porous Metal–Organic Framework through Post-Synthesis Modification and Studies on Suzuki and Stille Coupling Reactions under Heterogeneous Condition Saha, Debraj; Sen, Rupam; Maity, Tanmoy Langmuir, Vol. 29, Issue 9 https://doi.org/10.1021/la304147j	journal	February 2013
Perspective on Solvent Use in the Pharmaceutical Industry Constable, David J. C.; Jimenez-Gonzalez, Conchita; Henderson, Richard K. Organic Process Research & Development, Vol. 11, Issue 1 https://doi.org/10.1021/op060170h	journal	January 2007
Green chemistry Poliakoff, Martyn; Licence, Pete Nature, Vol. 450, Issue 7171 https://doi.org/10.1038/450810a	journal	December 2007
Recent advances in homogeneous nickel catalysis Tasker, Sarah Z.; Standley, Eric A.; Jamison, Timothy F. Nature, Vol. 509, Issue 7500 https://doi.org/10.1038/nature13274	journal	May 2014
Integration of accessible secondary metal sites into MOFs for H ₂ S removal Nickerl, Georg; Leistner, Matthias; Helten, Stella Inorg. Chem. Front., Vol. 1, Issue 4 https://doi.org/10.1039/C3QI00093A	journal	January 2014
A robust, catalytic metal–organic framework with open 2,2′-bipyridine sites Fei, Honghan; Cohen, Seth M. Chem. Commun., Vol. 50, Issue 37 https://doi.org/10.1039/C4CC01607F	journal	January 2014
Construction of a supported Ru complex on bifunctional MOF-253 for photocatalytic CO ₂ reduction under visible light Sun, Dengrong; Gao, Yanhong; Fu, Jinlong Chemical Communications, Vol. 51, Issue 13 https://doi.org/10.1039/C4CC09797A	journal	January 2015
Metal–organic frameworks catalyzed C–C and C–heteroatom coupling reactions Dhakshinamoorthy, Amarajothi; Asiri, Abdullah M.; Garcia, Hermenegildo Chemical Society Reviews, Vol. 44, Issue 7 https://doi.org/10.1039/C4CS00254G	journal	January 2015
Metal–organic frameworks: versatile heterogeneous catalysts for efficient catalytic organic transformations Chughtai, Adeel H.; Ahmad, Nazir; Younus, Hussein A. Chemical Society Reviews, Vol. 44, Issue 19 https://doi.org/10.1039/C4CS00395K	journal	January 2015
Carbonylative Sonogashira coupling of terminal alkynes with aryl iodides under atmospheric pressure of CO using Pd( ii )@MOF as the catalyst Bai, Cuihua; Jian, Siping; Yao, Xianfang Catalysis Science & Technology, Vol. 4, Issue 9 https://doi.org/10.1039/C4CY00488D	journal	January 2014
A molecular Pd( ii ) complex incorporated into a MOF as a highly active single-site heterogeneous catalyst for C–Cl bond activation Chen, Liyu; Rangan, Sylvie; Li, Jing Green Chemistry, Vol. 16, Issue 8 https://doi.org/10.1039/C4GC00314D	journal	January 2014
Enantioselective palladium catalyzed conjugate additions of ortho-substituted arylboronic acids to β,β-disubstituted cyclic enones: total synthesis of herbertenediol, enokipodin A and enokipodin B Buter, Jeffrey; Moezelaar, Renée; Minnaard, Adriaan J. Org. Biomol. Chem., Vol. 12, Issue 31 https://doi.org/10.1039/C4OB01085J	journal	January 2014
Mechanistic analysis of an asymmetric palladium-catalyzed conjugate addition of arylboronic acids to β-substituted cyclic enones Boeser, Cornelia L.; Holder, Jeffrey C.; Taylor, Buck L. H. Chemical Science, Vol. 6, Issue 3 https://doi.org/10.1039/C4SC03337J	journal	January 2015
Tackling poison and leach: catalysis by dangling thiol–palladium functions within a porous metal–organic solid Gui, Bo; Yee, Ka-Kit; Wong, Yan-Lung Chemical Communications, Vol. 51, Issue 32 https://doi.org/10.1039/C5CC00140D	journal	January 2015
Photocatalytic metal–organic frameworks for the aerobic oxidation of arylboronic acids Yu, Xiao; Cohen, Seth M. Chemical Communications, Vol. 51, Issue 48 https://doi.org/10.1039/C5CC01697E	journal	January 2015
N-Heterocyclic carbene (NHC) ligands and palladium in homogeneous cross-coupling catalysis: a perfect union Fortman, George C.; Nolan, Steven P. Chemical Society Reviews, Vol. 40, Issue 10 https://doi.org/10.1039/c1cs15088j	journal	January 2011
Catalysis by metal nanoparticles embedded on metal–organic frameworks Dhakshinamoorthy, Amarajothi; Garcia, Hermenegildo Chemical Society Reviews, Vol. 41, Issue 15 https://doi.org/10.1039/c2cs35047e	journal	January 2012
Ligand-free coupling of phenols and alcohols with aryl halides by a recyclable heterogeneous copper catalyst Wang, Man; Yuan, Bizhen; Ma, Tongmei RSC Advances, Vol. 2, Issue 13 https://doi.org/10.1039/c2ra20730c	journal	January 2012
High gas storage capacities and stepwise adsorption in a UiO type metal–organic framework incorporating Lewis basic bipyridyl sites Li, Liangjun; Tang, Sifu; Wang, Chao Chemical Communications, Vol. 50, Issue 18 https://doi.org/10.1039/c3cc48275h	journal	January 2014
Benign by design: catalyst-free in-water, on-water green chemical methodologies in organic synthesis Gawande, Manoj B.; Bonifácio, Vasco D. B.; Luque, Rafael Chemical Society Reviews, Vol. 42, Issue 12 https://doi.org/10.1039/c3cs60025d	journal	January 2013
Stabilizing unstable species through single-site isolation: a catalytically active TaV trialkyl in a porous organic polymer Tanabe, Kristine K.; Siladke, Nathan A.; Broderick, Erin M. Chemical Science, Vol. 4, Issue 6 https://doi.org/10.1039/c3sc22268c	journal	January 2013
Stability and degradation mechanisms of metal–organic frameworks containing the Zr6O4(OH)4 secondary building unit DeCoste, Jared B.; Peterson, Gregory W.; Jasuja, Himanshu Journal of Materials Chemistry A, Vol. 1, Issue 18 https://doi.org/10.1039/c3ta10662d	journal	January 2013
Clusters, surfaces, and catalysis Somorjai, G. A.; Contreras, A. M.; Montano, M. Proceedings of the National Academy of Sciences, Vol. 103, Issue 28 https://doi.org/10.1073/pnas.0507691103	journal	June 2006
Metal-Organic Frameworks as Selective or Chiral Oxidation Catalysts Leus, Karen; Liu, Ying-Ya; Van Der Voort, Pascal Catalysis Reviews, Vol. 56, Issue 1 https://doi.org/10.1080/01614940.2014.864145	journal	January 2014
Homogeneous Catalysis--New Approaches to Catalyst Separation, Recovery, and Recycling Cole-Hamilton, David J. Science, Vol. 299, Issue 5613, p. 1702-1706 https://doi.org/10.1126/science.1081881	journal	March 2003
Green Gold Catalysis Christensen, C. H.; Norskov, J. K. Science, Vol. 327, Issue 5963 https://doi.org/10.1126/science.1184203	journal	January 2010

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Single-site metal–organic framework catalysts for the oxidative coupling of arenes via C–H/C–H activation Van Velthoven, Niels; Waitschat, Steve; Chavan, Sachin M. Chemical Science, Vol. 10, Issue 12 https://doi.org/10.1039/c8sc05510f	journal	January 2019

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
aqueous media
conjugate addition
organic frameworks
palladium
quaternary center