Hydrogenation Reactions with Heterobimetallic Complexes

Abhyankar, Preshit C.; Thomas, Christine M.

doi:10.1002/anie.202416100

Title: Hydrogenation Reactions with Heterobimetallic Complexes

Journal Article · 07 November 2024 · Angewandte Chemie (International Edition)

DOI: https://doi.org/10.1002/anie.202416100 · OSTI ID:2476444

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Department of Chemistry and Biochemistry The Ohio State University 100 W. 18th Ave. 3109 Newman and Wolfrom Columbus Ohio 43210 United States

Abstract Hydrogenations are fundamentally and industrially important reactions that are atom economical paths to synthesize value‐added products from feedstock chemicals. The cooperative effects of two or more metal centers in multimetallic active sites is a successful strategy to activate small molecules and facilitate catalytic reactions, and this strategy has been recently applied to catalytic hydrogenation reactions. Furthermore, heterobimetallic complexes have been well‐documented to provide novel reaction pathways and improved selectivity, compared to their homo‐bimetallic and monometallic analogues. This minireview provides a historical perspective on the development of heterobimetallic catalysts for the hydrogenation of unsaturated substrates and describes recent developments in this burgeoning research area.

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Sponsoring Organization:: USDOE

Grant/Contract Number:: NONE; SC0019179

OSTI ID:: 2476444

Journal Information:: Angewandte Chemie (International Edition), Journal Name: Angewandte Chemie (International Edition) Journal Issue: 52 Vol. 63; ISSN 1433-7851

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

References (53)

Highly Polar Metal-Metal Bonds in “Early-Late” Heterodimetallic Complexes Gade, Lutz H. Angewandte Chemie International Edition, Vol. 39, Issue 15 https://doi.org/10.1002/1521-3773(20000804)39:15<2658::AID-ANIE2658>3.0.CO;2-C	journal	August 2000
LiAlH ₄ : From Stoichiometric Reduction to Imine Hydrogenation Catalysis Elsen, Holger; Färber, Christian; Ballmann, Gerd Angewandte Chemie International Edition, Vol. 57, Issue 24 https://doi.org/10.1002/anie.201803804	journal	May 2018
Selectivity Effects in Bimetallic Catalysis Mankad, Neal P. Chemistry - A European Journal, Vol. 22, Issue 17 https://doi.org/10.1002/chem.201505002	journal	February 2016
Insights into LiAlH ₄ Catalyzed Imine Hydrogenation Elsen, Holger; Langer, Jens; Ballmann, Gerd Chemistry – A European Journal, Vol. 27, Issue 1 https://doi.org/10.1002/chem.202003862	journal	November 2020
Unsaturated Bis(phosphido)‐bridged Heterobimetallic Polyhydrides via Dihydrogen Activation Thomas Baker, R.; Glassman, Timothy E.; Ovenall, Derick W. Israel Journal of Chemistry, Vol. 31, Issue 1 https://doi.org/10.1002/ijch.199100005	journal	January 1991
Hydrogenation of Edible oils Coenen, J. W. E. Journal of the American Oil Chemists' Society, Vol. 53, Issue 6Part2 https://doi.org/10.1007/BF02605727	journal	June 1976
Organocatalytic Transfer Hydrogenation and Hydrosilylation Reactions Herrera, Raquel P. Topics in Current Chemistry, Vol. 374, Issue 3 https://doi.org/10.1007/s41061-016-0032-4	journal	May 2016
Early-late heterobimetallics Stephan, Douglas W. Coordination Chemistry Reviews, Vol. 95, Issue 1 https://doi.org/10.1016/0010-8545(89)80002-5	journal	June 1989
Synthesis and catalytic activity of heterodinuclear Ru-Ir and Ru-Rh complexes. Crystal structure of [H(CO)(PPh3)2Ru(μ-Cl)(μ-pz)Ir(TFB)] (pz = pyrazolate, TFB = tetrafluorobenzobarrelene) García, Maria P.; López, Ana M.; Esteruelas, Miguel A. Journal of Organometallic Chemistry, Vol. 388, Issue 3 https://doi.org/10.1016/0022-328X(90)85382-9	journal	May 1990
Synthesis and evaluation of the catalytic properties of homo- and hetero-bimetallic complexes containing bridging diphenylphosphido ligands He, Zhongli; Lugan, Noël; Neibecker, Denis Journal of Organometallic Chemistry, Vol. 426, Issue 2 https://doi.org/10.1016/0022-328X(92)83047-L	journal	March 1992
Catalyst characteristics and performance in edible oil hydrogenation Balakos, Michael W.; Hernandez, Edgar E. Catalysis Today, Vol. 35, Issue 4 https://doi.org/10.1016/S0920-5861(96)00212-X	journal	April 1997
Catalytic conversion of biomass and plastic waste to alternative aviation fuels: A review Aghamiri, Ali Reza; Lahijani, Pooya Biomass and Bioenergy, Vol. 183 https://doi.org/10.1016/j.biombioe.2024.107120	journal	April 2024
Organic Reactions Enabled by Catalytically Active Metal–Metal Bonds Farley, Conner M.; Uyeda, Christopher Trends in Chemistry, Vol. 1, Issue 5 https://doi.org/10.1016/j.trechm.2019.04.002	journal	August 2019
Electrocatalytic Hydrogenation of Biomass-Derived Organics: A Review Akhade, Sneha A.; Singh, Nirala; Gutiérrez, Oliver Y. Chemical Reviews, Vol. 120, Issue 20 https://doi.org/10.1021/acs.chemrev.0c00158	journal	September 2020
Bimetallic Sites for Catalysis: From Binuclear Metal Sites to Bimetallic Nanoclusters and Nanoparticles Liu, Lichen; Corma, Avelino Chemical Reviews, Vol. 123, Issue 8 https://doi.org/10.1021/acs.chemrev.2c00733	journal	March 2023
Low-Valent Transition Metalate Anions in Synthesis, Small Molecule Activation, and Catalysis Landaeta, Vanessa R.; Horsley Downie, Thomas M.; Wolf, Robert Chemical Reviews, Vol. 124, Issue 4 https://doi.org/10.1021/acs.chemrev.3c00121	journal	February 2024
Mechanistic Insight into Synergistic Catalysis of Olefin Hydrogenation by a Hetero-Dinuclear Ru^II–Co^II Complex with Adjacent Reaction Sites Hong, Dachao; Ohgomori, Yuji; Shimoyama, Yoshihiro Inorganic Chemistry, Vol. 58, Issue 17 https://doi.org/10.1021/acs.inorgchem.9b02104	journal	August 2019
Alkaline Earth Metal Aluminates as Catalysts for Imine Hydrogenation Elsen, Holger; Langer, Jens; Wiesinger, Michael Organometallics, Vol. 39, Issue 23 https://doi.org/10.1021/acs.organomet.0c00226	journal	May 2020
Well-Defined Low-Valent Cobalt Complexes in Catalysis: An Overview Bories, Cassandre C.; Sodreau, Alexandre; Barbazanges, Marion Organometallics, Vol. 43, Issue 9 https://doi.org/10.1021/acs.organomet.4c00054	journal	April 2024
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
Catalytic Homogeneous Asymmetric Hydrogenation: Successes and Opportunities Seo, Chris S. G.; Morris, Robert H. Organometallics, Vol. 38, Issue 1 https://doi.org/10.1021/acs.organomet.8b00774	journal	December 2018
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 Organometallics, Vol. 38, Issue 18 https://doi.org/10.1021/acs.organomet.9b00331	journal	August 2019
Metal–Metal Bonds in Catalysis Powers, Ian G.; Uyeda, Christopher ACS Catalysis, Vol. 7, Issue 2 https://doi.org/10.1021/acscatal.6b02692	journal	December 2016
Cooperative Strategies for Catalytic Hydrogenation of Unsaturated Hydrocarbons Karunananda, Malkanthi K.; Mankad, Neal P. ACS Catalysis, Vol. 7, Issue 9 https://doi.org/10.1021/acscatal.7b02203	journal	August 2017
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
Multimetallic Catalysis Based on Heterometallic Complexes and Clusters Buchwalter, Paulin; Rosé, Jacky; Braunstein, Pierre Chemical Reviews, Vol. 115, Issue 1 https://doi.org/10.1021/cr500208k	journal	November 2014
Structure and Reactivity of Early−Late Heterobimetallic Complexes ^† Wheatley, Nigel; Kalck, Philippe Chemical Reviews, Vol. 99, Issue 12 https://doi.org/10.1021/cr980325m	journal	December 1999
Mechanism and Catalytic Impact of Ir–Ta Heterobimetallic and Ir–P Transition Metal/Main Group Interactions on Alkene Hydrogenation Zhang, Ying; Roberts, Samuel P.; Bergman, Robert G. ACS Catalysis, Vol. 5, Issue 3 https://doi.org/10.1021/cs501884j	journal	February 2015
Scope and mechanism of alkene hydrogenation/isomerization catalyzed by complexes of the type R2E(CH2)2M(CO)(L) (R = Cp, Me, Ph; E = phosphorus, tantalum; M = rhodium, iridium; L = CO, PPh3) Hostetler, Michael J.; Butts, Matthew D.; Bergman, Robert G. Journal of the American Chemical Society, Vol. 115, Issue 7 https://doi.org/10.1021/ja00060a024	journal	April 1993
Synthesis and reactivity of Cp2Ta(CH2)2Ir(CO)2: an early-late heterobimetallic complex that catalytically hydrogenates, isomerizes and hydrosilates alkenes Hostetler, Michael J.; Bergman, Robert G. Journal of the American Chemical Society, Vol. 112, Issue 23 https://doi.org/10.1021/ja00179a078	journal	November 1990
Synthesis of rhenium-alkene complexes from the reaction of the heterobimetallic dihydride C5H5(CO)2HRe-PtH(PPh3)2 with alkynes Casey, Charles P.; Rutter, Edward W. Journal of the American Chemical Society, Vol. 111, Issue 24 https://doi.org/10.1021/ja00206a024	journal	November 1989
Synthesis and physical properties of a dinuclear tantalum/cobalt radical with spin localized at one metal center Goldberg, Karen I.; Bergman, Robert G. Journal of the American Chemical Society, Vol. 110, Issue 14 https://doi.org/10.1021/ja00222a069	journal	July 1988
Rare-Earth Supported Nickel Catalysts for Alkyne Semihydrogenation: Chemo- and Regioselectivity Impacted by the Lewis Acidity and Size of the Support Ramirez, Bianca L.; Lu, Connie C. Journal of the American Chemical Society, Vol. 142, Issue 11 https://doi.org/10.1021/jacs.0c00905	journal	February 2020
Tuning Nickel with Lewis Acidic Group 13 Metalloligands for Catalytic Olefin Hydrogenation Cammarota, Ryan C.; Lu, Connie C. Journal of the American Chemical Society, Vol. 137, Issue 39 https://doi.org/10.1021/jacs.5b08313	journal	September 2015
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
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
Reactions of monoaza dienes with metal carbonyl complexes. 15. Heteronuclear monoaza dienyl complexes, isolobally related to cyclopentadienyl compounds Beers, Olaf C. P.; Bouman, Michiel M.; Komen, Agatha E. Organometallics, Vol. 12, Issue 2 https://doi.org/10.1021/om00026a017	journal	February 1993
Indirect cooperative effects leading to synergism in bimetallic homogeneous catalysts containing azolates as bridging ligands Esteruelas, Miguel A.; Garcia, Maria P.; Lopez, Ana M. Organometallics, Vol. 10, Issue 1 https://doi.org/10.1021/om00047a039	journal	January 1991
Synthesis and catalytic properties of heterobimetallic complexes of the tripod ligand HC(PPh2)3. X-ray molecular structures of [Rh(COD){HC(PPh2)3}Au(PPh3)](BF4)2 and [RhCu2{HC(PPh2)3}2(THF)2(CH3CN)2](BF4)2(F) El-Amouri, H.; Bahsoun, A. A.; Fischer, J. Organometallics, Vol. 10, Issue 10 https://doi.org/10.1021/om00056a031	journal	October 1991
The role of the metal-bound N–H functionality in Noyori-type molecular catalysts Dub, Pavel A.; Gordon, John C. Nature Reviews Chemistry, Vol. 2, Issue 12 https://doi.org/10.1038/s41570-018-0049-z	journal	November 2018
Evidence for enhancement of catalysis by a second metal in heterobinuclear complexes: X-ray structure of [H(CO)(PPh₃)₂Ru(bim)Rh(cod)](bim = 2,2′-bi-imidazolato, cod = cyclo-octa-1,5-diene) García, María P.; López, Ana M.; Esteruelas, Miguel A. J. Chem. Soc., Chem. Commun., Issue 12 https://doi.org/10.1039/C39880000793	journal	January 1988
Homogeneous hydrogenation of carbon dioxide to methanol Li, Yu-Nong; Ma, Ran; He, Liang-Nian Catal. Sci. Technol., Vol. 4, Issue 6 https://doi.org/10.1039/C3CY00564J	journal	January 2014
Bimetallic catalysis for C–C and C–X coupling reactions Pye, Dominic R.; Mankad, Neal P. Chemical Science, Vol. 8, Issue 3 https://doi.org/10.1039/C6SC05556G	journal	January 2017
Bis(bipyridine) ruthenium(ii) bis(phosphido) metalloligand: synthesis of heterometallic complexes and application to catalytic (E)-selective alkyne semi-hydrogenation Takemoto, Shin; Kitamura, Manami; Saruwatari, Shuhei Dalton Transactions, Vol. 48, Issue 4 https://doi.org/10.1039/C8DT04646H	journal	January 2019
Bimetallic nickel-lutetium complexes: tuning the properties and catalytic hydrogenation activity of the Ni site by varying the Lu coordination environment Ramirez, Bianca L.; Sharma, Prachi; Eisenhart, Reed J. Chemical Science, Vol. 10, Issue 11 https://doi.org/10.1039/C8SC04712J	journal	January 2019
Tuning metal–metal interactions for cooperative small molecule activation Wang, Qiuran; Brooks, Sam H.; Liu, Tianchang Chemical Communications, Vol. 57, Issue 23 https://doi.org/10.1039/D0CC07721F	journal	January 2021
Electrocatalytic hydrogenation and depolymerization pathways for lignin valorization: toward mild synthesis of chemicals and fuels from biomass Wijaya, Yanuar Philip; Smith, Kevin J.; Kim, Chang Soo Green Chemistry, Vol. 22, Issue 21 https://doi.org/10.1039/D0GC02782K	journal	January 2020
Cooperative activation of carbon–hydrogen bonds by heterobimetallic systems Lachguar, Abdelhak; Pichugov, Andrey V.; Neumann, Till Dalton Transactions, Vol. 53, Issue 4 https://doi.org/10.1039/D3DT03571A	journal	January 2024
Syntheses and reactivities of hydrosulfido- or sulfido-bridged heterobimetallic complexes containing Group 6 and Group 9 metals Kato, Hiroko; Seino, Hidetake; Mizobe, Yasushi Journal of the Chemical Society, Dalton Transactions, Issue 7 https://doi.org/10.1039/b108227m	journal	March 2002
Recent advances in the catalytic asymmetric synthesis of β-amino acids Weiner, Barbara; Szymański, Wiktor; Janssen, Dick B. Chemical Society Reviews, Vol. 39, Issue 5 https://doi.org/10.1039/b919599h	journal	January 2010
“Frustrated Lewis pair” hydrogenations Stephan, Douglas W. Organic & Biomolecular Chemistry, Vol. 10, Issue 30 https://doi.org/10.1039/c2ob25339a	journal	January 2012
Catalytic Applications of Early/Late Heterobimetallic Complexes Cooper, Benjamin G.; Napoline, J. Wesley; Thomas, Christine M. Catalysis Reviews, Vol. 54, Issue 1 https://doi.org/10.1080/01614940.2012.619931	journal	January 2012
Added Complexity!—Mechanistic Aspects of Heterobimetallic Complexes for Application in Homogeneous Catalysis Fickenscher, Zeno; Hey-Hawkins, Evamarie Molecules, Vol. 28, Issue 10 https://doi.org/10.3390/molecules28104233	journal	May 2023

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