Mechanistic Study on the Origin of the Trans Selectivity in Alkyne Semihydrogenation by a Heterobimetallic Rhodium–Gallium Catalyst in a Metal–Organic Framework

Desai, Sai Puneet; Ye, Jingyun; Islamoglu, Timur; Farha, Omar K.; Lu, Connie C.

doi:10.1021/acs.organomet.9b00331

Mechanistic Study on the Origin of the Trans Selectivity in Alkyne Semihydrogenation by a Heterobimetallic Rhodium–Gallium Catalyst in a Metal–Organic Framework

Journal Article · 16 August 2019 · Organometallics

DOI:https://doi.org/10.1021/acs.organomet.9b00331· OSTI ID:1611930

Desai, Sai Puneet; ; ^[1]; ^[1];

International Institute of Nanotechnology and Department of Chemistry, Northwestern University, Evanston, Illinois 60208, United States

Not provided.

Research Organization:: Energy Frontier Research Centers (EFRC) (United States). Energy Frontier Research Center for Inorganometallic Catalyst Design (ICDC); Univ. of Minnesota, Minneapolis, MN (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

DOE Contract Number:: SC0012702

OSTI ID:: 1611930

Journal Information:: Organometallics, Vol. 38, Issue 18; ISSN 0276-7333

Publisher:: American Chemical Society

Country of Publication:: United States

Language:: English

References (66)

Engineering Metal Organic Frameworks for Heterogeneous Catalysis Corma, A.; García, H.; Llabrés i Xamena, F. X. Chemical Reviews, Vol. 110, Issue 8, p. 4606-4655 https://doi.org/10.1021/cr9003924	journal	August 2010
Catalysis by Metal Organic Frameworks: Perspective and Suggestions for Future Research Yang, Dong; Gates, Bruce C. ACS Catalysis, Vol. 9, Issue 3 https://doi.org/10.1021/acscatal.8b04515	journal	January 2019
Applications of metal–organic frameworks in heterogeneous supramolecular catalysis Liu, Jiewei; Chen, Lianfen; Cui, Hao Chemical Society Reviews, Vol. 43, Issue 16, p. 6011-6061 https://doi.org/10.1039/C4CS00094C	journal	January 2014
Postsynthetic modification of metal–organic frameworks—a progress report Tanabe, Kristine K.; Cohen, Seth M. Chem. Soc. Rev., Vol. 40, Issue 2 https://doi.org/10.1039/C0CS00031K	journal	January 2011
Metal–Organic Frameworks in Solid–Gas Phase Catalysis Wang, Cheng; An, Bing; Lin, Wenbin ACS Catalysis, Vol. 9, Issue 1 https://doi.org/10.1021/acscatal.8b04055	journal	November 2018
Metal–organic framework materials as catalysts Lee, JeongYong; Farha, Omar K.; Roberts, John Chemical Society Reviews, Vol. 38, Issue 5, p. 1450-1459 https://doi.org/10.1039/b807080f	journal	January 2009
The Chemistry and Applications of Metal-Organic Frameworks Furukawa, H.; Cordova, K. E.; O'Keeffe, M. Science, Vol. 341, Issue 6149, p. 1230444-1230444 https://doi.org/10.1126/science.1230444	journal	August 2013
Toward “metalloMOFzymes”: Metal–Organic Frameworks with Single-Site Metal Catalysts for Small-Molecule Transformations Cohen, Seth M.; Zhang, Zhenjie; Boissonnault, Jake A. Inorganic Chemistry, Vol. 55, Issue 15 https://doi.org/10.1021/acs.inorgchem.6b00828	journal	May 2016
Postsynthetic Methods for the Functionalization of Metal–Organic Frameworks Cohen, Seth M. Chemical Reviews, Vol. 112, Issue 2, p. 970-1000 https://doi.org/10.1021/cr200179u	journal	September 2011
Catalytic chemoselective functionalization of methane in a metal−organic framework Zhang, Xuan; Huang, Zhiyuan; Ferrandon, Magali Nature Catalysis, Vol. 1, Issue 5 https://doi.org/10.1038/s41929-018-0069-6	journal	May 2018
Fine-Tuning the Activity of Metal–Organic Framework-Supported Cobalt Catalysts for the Oxidative Dehydrogenation of Propane Li, Zhanyong; Peters, Aaron W.; Platero-Prats, Ana E. Journal of the American Chemical Society, Vol. 139, Issue 42 https://doi.org/10.1021/jacs.7b09365	journal	October 2017
Chemoselective single-site Earth-abundant metal catalysts at metal–organic framework nodes Manna, Kuntal; Ji, Pengfei; Lin, Zekai Nature Communications, Vol. 7, Issue 1 https://doi.org/10.1038/ncomms12610	journal	August 2016
Single-Site Organozirconium Catalyst Embedded in a Metal–Organic Framework Klet, Rachel C.; Tussupbayev, Samat; Borycz, Joshua Journal of the American Chemical Society, Vol. 137, Issue 50 https://doi.org/10.1021/jacs.5b11350	journal	December 2015
Bioinspired Metal–Organic Framework for Trace CO 2 Capture Bien, Caitlin E.; Chen, Kai K.; Chien, Szu-Chia Journal of the American Chemical Society, Vol. 140, Issue 40 https://doi.org/10.1021/jacs.8b06109	journal	September 2018
Oxidation of ethane to ethanol by N2O in a metal–organic framework with coordinatively unsaturated iron(II) sites Xiao, Dianne J.; Bloch, Eric D.; Mason, Jarad A. Nature Chemistry, Vol. 6, Issue 7 https://doi.org/10.1038/nchem.1956	journal	May 2014
The role of reticular chemistry in the design of CO2 reduction catalysts Diercks, Christian S.; Liu, Yuzhong; Cordova, Kyle E. Nature Materials, Vol. 17, Issue 4 https://doi.org/10.1038/s41563-018-0033-5	journal	February 2018
Zirconium Metal–Organic Frameworks Assembled from Pd and Pt P ^N N ^N P Pincer Complexes: Synthesis, Postsynthetic Modification, and Lewis Acid Catalysis Reiner, Benjamin R.; Mucha, Neil T.; Rothstein, Anna Inorganic Chemistry, Vol. 57, Issue 5 https://doi.org/10.1021/acs.inorgchem.7b03063	journal	February 2018
Tuning Zr ₆ Metal–Organic Framework (MOF) Nodes as Catalyst Supports: Site Densities and Electron-Donor Properties Influence Molecular Iridium Complexes as Ethylene Conversion Catalysts Yang, Dong; Odoh, Samuel O.; Borycz, Joshua ACS Catalysis, Vol. 6, Issue 1 https://doi.org/10.1021/acscatal.5b02243	journal	December 2015
Methane Oxidation to Methanol Catalyzed by Cu-Oxo Clusters Stabilized in NU-1000 Metal–Organic Framework Ikuno, Takaaki; Zheng, Jian; Vjunov, Aleksei Journal of the American Chemical Society, Vol. 139, Issue 30 https://doi.org/10.1021/jacs.7b02936	journal	July 2017
Single-Site Cobalt Catalysts at New Zr ₈ (μ ₂ -O) ₈ (μ ₂ -OH) ₄ Metal-Organic Framework Nodes for Highly Active Hydrogenation of Alkenes, Imines, Carbonyls, and Heterocycles Ji, Pengfei; Manna, Kuntal; Lin, Zekai Journal of the American Chemical Society, Vol. 138, Issue 37 https://doi.org/10.1021/jacs.6b06759	journal	September 2016
Metal–Organic Framework Nodes Support Single-Site Magnesium–Alkyl Catalysts for Hydroboration and Hydroamination Reactions Manna, Kuntal; Ji, Pengfei; Greene, Francis X. Journal of the American Chemical Society, Vol. 138, Issue 24 https://doi.org/10.1021/jacs.6b03689	journal	June 2016
A Metal-Organic Framework with Exceptional Activity for C−H Bond Amination Wang, Le; Agnew, Douglas W.; Yu, Xiao Angewandte Chemie International Edition, Vol. 57, Issue 2 https://doi.org/10.1002/anie.201709420	journal	December 2017
Porphyrinic Metal–Organic Frameworks Installed with Brønsted Acid Sites for Efficient Tandem Semisynthesis of Artemisinin Feng, Liang; Wang, Ying; Yuan, Shuai ACS Catalysis, Vol. 9, Issue 6 https://doi.org/10.1021/acscatal.8b04960	journal	March 2019
Aperture-Opening Encapsulation of a Transition Metal Catalyst in a Metal–Organic Framework for CO ₂ Hydrogenation Li, Zhehui; Rayder, Thomas M.; Luo, Lianshun Journal of the American Chemical Society, Vol. 140, Issue 26 https://doi.org/10.1021/jacs.8b04047	journal	June 2018
Heterogeneous Catalysis: Understanding for Designing, and Designing for Applications Corma, Avelino Angewandte Chemie International Edition, Vol. 55, Issue 21 https://doi.org/10.1002/anie.201601231	journal	April 2016
Mechanism of Single-Site Molecule-Like Catalytic Ethylene Dimerization in Ni-MFU-4 l Metzger, Eric D.; Comito, Robert J.; Hendon, Christopher H. Journal of the American Chemical Society, Vol. 139, Issue 2 https://doi.org/10.1021/jacs.6b10300	journal	January 2017
Probing the Evolution of Palladium Species in Pd@MOF Catalysts during the Heck Coupling Reaction: An Operando X-ray Absorption Spectroscopy Study Yuan, Ning; Pascanu, Vlad; Huang, Zhehao Journal of the American Chemical Society, Vol. 140, Issue 26 https://doi.org/10.1021/jacs.8b03505	journal	June 2018
Vapor-Phase Metalation by Atomic Layer Deposition in a Metal–Organic Framework Mondloch, Joseph E.; Bury, Wojciech; Fairen-Jimenez, David Journal of the American Chemical Society, Vol. 135, Issue 28, p. 10294-10297 https://doi.org/10.1021/ja4050828	journal	May 2013
Defining the Proton Topology of the Zr₆-Based Metal–Organic Framework NU-1000 Planas, Nora; Mondloch, Joseph E.; Tussupbayev, Samat The Journal of Physical Chemistry Letters, Vol. 5, Issue 21, p. 3716-3723 https://doi.org/10.1021/jz501899j	journal	October 2014
Installing Heterobimetallic Cobalt–Aluminum Single Sites on a Metal Organic Framework Support Thompson, Anthony B.; Pahls, Dale R.; Bernales, Varinia Chemistry of Materials, Vol. 28, Issue 18 https://doi.org/10.1021/acs.chemmater.6b03244	journal	September 2016
Assembly of dicobalt and cobalt–aluminum oxide clusters on metal–organic framework and nanocast silica supports Desai, Sai Puneet; Malonzo, Camille D.; Webber, Thomas Faraday Discussions, Vol. 201 https://doi.org/10.1039/C7FD00055C	journal	January 2017
Role of a Modulator in the Synthesis of Phase-Pure NU-1000 Webber, Thomas E.; Liu, Wei-Guang; Desai, Sai Puneet ACS Applied Materials & Interfaces, Vol. 9, Issue 45 https://doi.org/10.1021/acsami.7b11348	journal	November 2017
Well-Defined Rhodium–Gallium Catalytic Sites in a Metal–Organic Framework: Promoter-Controlled Selectivity in Alkyne Semihydrogenation to E -Alkenes Desai, Sai Puneet; Ye, Jingyun; Zheng, Jian Journal of the American Chemical Society, Vol. 140, Issue 45 https://doi.org/10.1021/jacs.8b08550	journal	October 2018
In situ 1H-PHIP-NMR studies of the stereoselective hydrogenation of alkynes to ( E)-alkenes catalyzed by a homogeneous [Cp*Ru]+ catalyst Schleyer, Dana; Niessen, Heiko G.; Bargon, Joachim New Journal of Chemistry, Vol. 25, Issue 3 https://doi.org/10.1039/b007201j	journal	January 2001
Iron Pincer Complex Catalyzed, Environmentally Benign, E -Selective Semi-Hydrogenation of Alkynes Srimani, Dipankar; Diskin-Posner, Yael; Ben-David, Yehoshoa Angewandte Chemie, Vol. 125, Issue 52 https://doi.org/10.1002/ange.201306629	journal	November 2013
Selective Hydrogenation of Functionalized Alkynes to ( E )-Alkenes, Using Ordered Alloys as Catalysts Furukawa, Shinya; Komatsu, Takayuki ACS Catalysis, Vol. 6, Issue 3 https://doi.org/10.1021/acscatal.5b02953	journal	February 2016
Alkyne Semihydrogenation with a Well-Defined Nonclassical Co–H ₂ Catalyst: A H ₂ Spin on Isomerization and E -Selectivity Tokmic, Kenan; Fout, Alison R. Journal of the American Chemical Society, Vol. 138, Issue 41 https://doi.org/10.1021/jacs.6b08128	journal	October 2016
A Functional-Group-Tolerant Catalytic trans Hydrogenation of Alkynes Radkowski, Karin; Sundararaju, Basker; Fürstner, Alois Angewandte Chemie International Edition, Vol. 52, Issue 1 https://doi.org/10.1002/anie.201205946	journal	September 2012
E -Selective Semi-Hydrogenation of Alkynes by Heterobimetallic Catalysis Karunananda, Malkanthi K.; Mankad, Neal P. Journal of the American Chemical Society, Vol. 137, Issue 46 https://doi.org/10.1021/jacs.5b10357	journal	November 2015
An Alkene‐Promoted Borane‐Catalyzed Highly Stereoselective Hydrogenation of Alkynes to Give Z ‐ and E ‐Alkenes Liu, Yongbing; Hu, Lianrui; Chen, Hui Chemistry – A European Journal, Vol. 21, Issue 8 https://doi.org/10.1002/chem.201405388	journal	January 2015
Direct trans -Selective Ruthenium-Catalyzed Reduction of Alkynes in Two-Chamber Reactors and Continuous Flow Neumann, Karoline T.; Klimczyk, Sebastian; Burhardt, Mia N. ACS Catalysis, Vol. 6, Issue 7 https://doi.org/10.1021/acscatal.6b01045	journal	June 2016
Cooperative H ₂ Activation across a Metal–Metal Multiple Bond and Hydrogenation Reactions Catalyzed by a Zr/Co Heterobimetallic Complex Gramigna, Kathryn M.; Dickie, Diane A.; Foxman, Bruce M. ACS Catalysis, Vol. 9, Issue 4 https://doi.org/10.1021/acscatal.8b04390	journal	March 2019
Efficient Catalytic System for Synthesis of trans -Stilbene from Diphenylacetylene Using Rh-Based Intermetallic Compounds Furukawa, Shinya; Yokoyama, Akira; Komatsu, Takayuki ACS Catalysis, Vol. 4, Issue 10 https://doi.org/10.1021/cs500947d	journal	September 2014
Intermetallic Ni _x M _y ( M = Ga and Sn) Nanocrystals: A Non-precious Metal Catalyst for Semi-Hydrogenation of Alkynes Liu, Yuxi; Liu, Xiangwen; Feng, Quanchen Advanced Materials, Vol. 28, Issue 23 https://doi.org/10.1002/adma.201600603	journal	April 2016
Selective Semihydrogenation of Alkynes with N-Graphitic-Modified Cobalt Nanoparticles Supported on Silica Chen, Feng; Kreyenschulte, Carsten; Radnik, Jörg ACS Catalysis, Vol. 7, Issue 3 https://doi.org/10.1021/acscatal.6b03140	journal	January 2017
Half-Sandwich Ruthenium Carbene Complexes Link trans -Hydrogenation and gem -Hydrogenation of Internal Alkynes Guthertz, Alexandre; Leutzsch, Markus; Wolf, Lawrence M. Journal of the American Chemical Society, Vol. 140, Issue 8 https://doi.org/10.1021/jacs.8b00665	journal	February 2018
Hydrogenation of carbon–carbon multiple bonds: chemo-, regio- and stereo-selectivity Molnár, Árpád; Sárkány, Antal; Varga, Mónika Journal of Molecular Catalysis A: Chemical, Vol. 173, Issue 1-2 https://doi.org/10.1016/S1381-1169(01)00150-9	journal	September 2001
Nickel-catalyzed (E)-selective semihydrogenation of internal alkynes with hypophosphorous acid Chen, Tieqiao; Xiao, Jing; Zhou, Yongbo Journal of Organometallic Chemistry, Vol. 749 https://doi.org/10.1016/j.jorganchem.2013.09.023	journal	January 2014
Heterobimetallic H ₂ Addition and Alkene/Alkane Elimination Reactions Related to the Mechanism of E -Selective Alkyne Semihydrogenation Karunananda, Malkanthi K.; Mankad, Neal P. Organometallics, Vol. 36, Issue 1 https://doi.org/10.1021/acs.organomet.6b00356	journal	June 2016
Formation of Ruthenium Carbenes by gem -Hydrogen Transfer to Internal Alkynes: Implications for Alkyne trans -Hydrogenation Leutzsch, Markus; Wolf, Larry M.; Gupta, Puneet Angewandte Chemie International Edition, Vol. 54, Issue 42 https://doi.org/10.1002/anie.201506075	journal	August 2015
Dynamically Bifurcating Hydride Transfer Mechanism and Origin of Inverse Isotope Effect for Heterodinuclear AgRu-Catalyzed Alkyne Semihydrogenation Zhang, Ying; Karunananda, Malkanthi K.; Yu, Hsien-Cheng ACS Catalysis, Vol. 9, Issue 3 https://doi.org/10.1021/acscatal.8b04130	journal	February 2019
Rhodium-Catalyzed Selective Partial Hydrogenation of Alkynes Luo, Jingwei; Theron, Robin; Sewell, Laura J. Organometallics, Vol. 34, Issue 12 https://doi.org/10.1021/acs.organomet.5b00322	journal	June 2015
Kinetic and Spectroscopic Studies of the [Palladium(Ar-bian)]-Catalyzed Semi-Hydrogenation of 4-Octyne Kluwer, Alexander M.; Koblenz, Tehila S.; Jonischkeit, Thorsten Journal of the American Chemical Society, Vol. 127, Issue 44 https://doi.org/10.1021/ja052729j	journal	November 2005
Revisiting the structural homogeneity of NU-1000, a Zr-based metal–organic framework Islamoglu, Timur; Otake, Ken-ichi; Li, Peng CrystEngComm, Vol. 20, Issue 39 https://doi.org/10.1039/C8CE00455B	journal	January 2018
Role of the Metal in the Bonding and Properties of Bimetallic Complexes Involving Manganese, Iron, and Cobalt Tereniak, Stephen J.; Carlson, Rebecca K.; Clouston, Laura J. Journal of the American Chemical Society, Vol. 136, Issue 5 https://doi.org/10.1021/ja409016w	journal	November 2013
Mechanism of Ti-Catalyzed Oxidative Nitrene Transfer in [2 + 2 + 1] Pyrrole Synthesis from Alkynes and Azobenzene Davis-Gilbert, Zachary W.; Wen, Xuelan; Goodpaster, Jason D. Journal of the American Chemical Society, Vol. 140, Issue 23 https://doi.org/10.1021/jacs.8b03546	journal	May 2018
cp2k: atomistic simulations of condensed matter systems Hutter, Jürg; Iannuzzi, Marcella; Schiffmann, Florian Wiley Interdisciplinary Reviews: Computational Molecular Science, Vol. 4, Issue 1 https://doi.org/10.1002/wcms.1159	journal	June 2013
Generalized Gradient Approximation Made Simple Perdew, John P.; Burke, Kieron; Ernzerhof, Matthias Physical Review Letters, Vol. 77, Issue 18, p. 3865-3868 https://doi.org/10.1103/PhysRevLett.77.3865	journal	October 1996
A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu Grimme, Stefan; Antony, Jens; Ehrlich, Stephan The Journal of Chemical Physics, Vol. 132, Issue 15 https://doi.org/10.1063/1.3382344	journal	April 2010
Separable dual-space Gaussian pseudopotentials Goedecker, S.; Teter, M.; Hutter, J. Physical Review B, Vol. 54, Issue 3 https://doi.org/10.1103/PhysRevB.54.1703	journal	July 1996
Single Ni atoms and Ni4 clusters have similar catalytic activity for ethylene dimerization Ye, Jingyun; Gagliardi, Laura; Cramer, Christopher J. Journal of Catalysis, Vol. 354 https://doi.org/10.1016/j.jcat.2017.08.011	journal	October 2017
A climbing image nudged elastic band method for finding saddle points and minimum energy paths Henkelman, Graeme; Uberuaga, Blas P.; Jónsson, Hannes The Journal of Chemical Physics, Vol. 113, Issue 22, p. 9901-9904 https://doi.org/10.1063/1.1329672	journal	December 2000
Chemically Meaningful Atomic Charges That Reproduce the Electrostatic Potential in Periodic and Nonperiodic Materials Manz, Thomas A.; Sholl, David S. Journal of Chemical Theory and Computation, Vol. 6, Issue 8 https://doi.org/10.1021/ct100125x	journal	July 2010
Improved Atoms-in-Molecule Charge Partitioning Functional for Simultaneously Reproducing the Electrostatic Potential and Chemical States in Periodic and Nonperiodic Materials Manz, Thomas A.; Sholl, David S. Journal of Chemical Theory and Computation, Vol. 8, Issue 8 https://doi.org/10.1021/ct3002199	journal	July 2012
Introducing DDEC6 atomic population analysis: part 1. Charge partitioning theory and methodology Manz, Thomas A.; Limas, Nidia Gabaldon RSC Advances, Vol. 6, Issue 53 https://doi.org/10.1039/C6RA04656H	journal	January 2016
Introducing DDEC6 atomic population analysis: part 2. Computed results for a wide range of periodic and nonperiodic materials Limas, Nidia Gabaldon; Manz, Thomas A. RSC Advances, Vol. 6, Issue 51 https://doi.org/10.1039/C6RA05507A	journal	January 2016

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