Scope and Mechanism of Cooperativity at the Intersection of Organometallic and Supramolecular Catalysis

Levin, Mark D.; Kaphan, David M.; Hong, Cynthia M.; Bergman, Robert G.; Raymond, Kenneth N.; Toste, F. Dean

doi:10.1021/jacs.6b05442

Title: Scope and Mechanism of Cooperativity at the Intersection of Organometallic and Supramolecular Catalysis

Journal Article · 26 July 2016 · Journal of the American Chemical Society

DOI: https://doi.org/10.1021/jacs.6b05442 · OSTI ID:1464140

Levin, Mark D. ^[1]; Kaphan, David M. ^[1]; Hong, Cynthia M. ^[1]; Bergman, Robert G. ^[1]; Raymond, Kenneth N. ^[1]; Toste, F. Dean ^[1]

Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Chemical Sciences Division; Univ. of California, Berkeley, CA (United States). Dept. of Chemistry

Here, the scope and mechanism of the microenvironment-catalyzed C(sp³)-C(sp³) reductive elimination from transition metal complexes [Au(III), Pt(IV)] is explored. Experiments detailing the effect of structural perturbation of neutral and anionic spectator ligands, reactive alkyl ligands, solvent, and catalyst structure are disclosed. Indirect evidence for a coordinatively unsaturated encapsulated cationic intermediate is garnered via observation of several inactive donor-arrested inclusion complexes, including a crystallographically characterized encapsulated Au(III) cation. Finally, based on stoichiometric experiments under catalytically relevant conditions, a detailed mechanism is outlined for the dual supramolecular and platinum-catalyzed C-C coupling between methyl iodide and tetramethyltin. Determination of major platinum species present under catalytic conditions and subsequent investigation of their chemistry reveals an unexpected interplay between cis-trans isomerism and the supramolecular catalyst in a Pt(II)/Pt(IV) cycle, as well as several off-cycle reactions.

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Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences, and Biosciences Division; National Institutes of Health (NIH); National Science Foundation (NSF)

Grant/Contract Number:: AC02-05CH11231; R01 GM073932; DGE 1106400

OSTI ID:: 1464140

Journal Information:: Journal of the American Chemical Society, Vol. 138, Issue 30; Related Information: © 2016 American Chemical Society.; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 77 works

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Dynamics of Assembly and Guest Exchange in the Tennis Ball Szabo, Tomas; Hilmersson, Göran; Rebek, Julius Journal of the American Chemical Society, Vol. 120, Issue 24 https://doi.org/10.1021/ja980161r	journal	June 1998
A nanometre-sized hexahedral coordination capsule assembled from 24 components Takeda, Nobuhiro; Umemoto, Kazuhiko; Yamaguchi, Kentaro Nature, Vol. 398, Issue 6730 https://doi.org/10.1038/19734	journal	April 1999
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High-definition self-assemblies driven by the hydrophobic effect: synthesis and properties of a supramolecular nanocapsule Liu, Simin; Gibb, Bruce C. Chemical Communications, Issue 32 https://doi.org/10.1039/b805446k	journal	January 2008
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Encapsulation of a Quinhydrone Cofactor in the Inner Pocket of Cobalt Triangular Prisms: Combined Light-Driven Reduction of Protons and Hydrogenation of Nitrobenzene Zhao, Liang; Wei, Jianwei; Zhang, Jing Angewandte Chemie International Edition, Vol. 56, Issue 48 https://doi.org/10.1002/anie.201707676	journal	November 2017
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Coordination‐Cage‐Catalysed Hydrolysis of Organophosphates: Cavity‐ or Surface‐Based? Taylor, Christopher G. P.; Metherell, Alexander J.; Argent, Stephen P. Chemistry – A European Journal, Vol. 26, Issue 14 https://doi.org/10.1002/chem.201904708	journal	February 2020
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Catalytic Intramolecular Cycloaddition Reactions by Using a Discrete Molecular Architecture Roy, Bijan; Devaraj, Anthonisamy; Saha, Rupak Chemistry - A European Journal, Vol. 23, Issue 62 https://doi.org/10.1002/chem.201702507	journal	October 2017
Programmable self-assembly of water-soluble organo-heterometallic cages [M ₁₂ M′ ₄ L ₁₂ ] using 3-(3,5-dimethyl-1H-pyrazol-4-yl)pentane-2,4-dione (H ₂ L) Chen, Zi-Man; Cui, Yu; Jiang, Xuan-Feng Chemical Communications, Vol. 53, Issue 30 https://doi.org/10.1039/c7cc00425g	journal	January 2017
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Measuring ion-pairing and hydration in variable charge supramolecular cages with microwave microfluidics Stelson, Angela C.; Hong, Cynthia M.; Groenenboom, Mitchell C. Communications Chemistry, Vol. 2, Issue 1 https://doi.org/10.1038/s42004-019-0157-9	journal	May 2019
Strategies for binding multiple guests in metal–organic cages Rizzuto, Felix J.; von Krbek, Larissa K. S.; Nitschke, Jonathan R. Nature Reviews Chemistry, Vol. 3, Issue 4 https://doi.org/10.1038/s41570-019-0085-3	journal	March 2019
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Encapsulation of a Quinhydrone Cofactor in the Inner Pocket of Cobalt Triangular Prisms: Combined Light-Driven Reduction of Protons and Hydrogenation of Nitrobenzene Zhao, Liang; Wei, Jianwei; Zhang, Jing Angewandte Chemie, Vol. 129, Issue 48 https://doi.org/10.1002/ange.201707676	journal	November 2017
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Elucidating the Importance of Hydrochloric Acid as a Cocatalyst for Resorcinarene-Capsule-Catalyzed reactions Köster, J.; Tiefenbacher, K. Wiley https://doi.org/10.5451/unibas-ep68400	text	January 2018
Sesquiterpene Cyclizations inside the Hexameric Resorcinarene Capsule: Total Synthesis of δ‐Selinene and Mechanistic Studies Zhang, Qi; Tiefenbacher, Konrad Wiley https://doi.org/10.5451/unibas-ep75126	text	January 2019
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Cover Feature: Coordination‐Cage‐Catalysed Hydrolysis of Organophosphates: Cavity‐ or Surface‐Based? (Chem. Eur. J. 14/2020) Taylor, Christopher G. P.; Metherell, Alexander J.; Argent, Stephen P. Chemistry – A European Journal, Vol. 26, Issue 14 https://doi.org/10.1002/chem.201905616	journal	February 2020
A Zn ₄ L ₆ Capsule with Enhanced Catalytic C−C Bond Formation Activity upon C ₆₀ Binding Lu, Zhenpin; Lavendomme, Roy; Burghaus, Olaf Apollo - University of Cambridge Repository https://doi.org/10.17863/cam.39564	text	January 2019
Interplay of Water and a Supramolecular Capsule for Catalysis of Reductive Elimination Reaction from Gold Welborn, Valerie Vaissier; Li, Wan-Lu; Head-Gordon, Teresa arXiv https://doi.org/10.48550/arxiv.1908.10991	preprint	January 2019
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Coordination‐Cage‐Catalysed Hydrolysis of Organophosphates: Cavity‐ or Surface‐Based? Taylor, Christopher G. P.; Metherell, Alexander J.; Argent, Stephen P. Chemistry – A European Journal, Vol. 26, Issue 14 https://doi.org/10.1002/chem.201904708	journal	February 2020
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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
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CCDC 1505081: Experimental Crystal Structure Determination: OVUHOE : diiodo-dimethyl-bis(trimethylphosphine)-platinum Levin, Mark D.; Kaphan, David M.; Hong, Cynthia M. https://doi.org/10.5517/ccdc.csd.cc1mj50b The current record is supplemented by this dataset	dataset	September 2016
CCDC 1505082: Experimental Crystal Structure Determination: OVUHUK : tris(Oxonium) octa-potassium hexakis(μ-3,3'-(naphthalene-1,5-diyldicarbamoyl)bis(benzene-1,2-diolato))-tetra-gallium dimethyl-bis(trimethylphosphine)-gold(iii) clathrate unknown solvate tridecahydrate Levin, Mark D.; Kaphan, David M.; Hong, Cynthia M. https://doi.org/10.5517/ccdc.csd.cc1mj51c The current record is supplemented by this dataset	dataset	September 2016