Activation of Low-Valent, Multiply M–M Bonded Group VI Dimers toward Catalytic Olefin Metathesis via Surface Organometallic Chemistry

Chapovetsky, Alon; Langeslay, Ryan R.; Celik, Gokhan; Perras, Frédéric A.; Pruski, Marek; Ferrandon, Magali S.; Wegener, Evan C.; Kim, Hacksung; Dogan, Fulya; Wen, Jianguo; Khetrapal, Navneet; Sharma, Prachi; White, Jacob; Kropf, A. Jeremy; Sattelberger, Alfred P.; Kaphan, David M.; Delferro, Massimiliano

doi:10.1021/acs.organomet.9b00787

Title: Activation of Low-Valent, Multiply M–M Bonded Group VI Dimers toward Catalytic Olefin Metathesis via Surface Organometallic Chemistry

Journal Article · Thu Feb 13 00:00:00 EST 2020 · Organometallics

DOI:https://doi.org/10.1021/acs.organomet.9b00787· OSTI ID:1632171

Chapovetsky, Alon ^[1];

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^[2];

^[2]; Ferrandon, Magali S. ^[1]; Wegener, Evan C. ^[1];

^[3];

^[1];

^[4]; Khetrapal, Navneet ^[5];

^[5]; White, Jacob ^[5]; Kropf, A. Jeremy ^[1]; Sattelberger, Alfred P. ^[1];

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Argonne National Lab. (ANL), Argonne, IL (United States). Chemical Sciences and Engineering Division
Ames Lab., Ames, IA (United States)
Argonne National Lab. (ANL), Argonne, IL (United States). Chemical Sciences and Engineering Division; ; Northwestern Univ., Evanston, IL (United States). Center for Catalysis and Surface Science
Argonne National Lab. (ANL), Argonne, IL (United States). Center for Nanoscale Materials
Univ. of Minnesota, Minneapolis, MN (United States)

Olefin metathesis is a broadly employed reaction with applications that range from fine chemicals to materials and petrochemicals. The design and investigation of olefin metathesis catalysts have been ongoing for over half a century, with advancements made in terms of activity, stability, and selectivity. Immobilization of organometallic complexes onto solid supports such as silica or alumina is a promising strategy for catalyst heterogenization, often resulting in increased activity and stability. Consequently, a broad range of early transition metal catalysts bearing alkyl, oxide/alkoxide, and amide ligands have been grafted onto silica and their reactivities investigated. In this paper, we report a series of silica-supported tungsten and molybdenum dimers (X₃M≡MX_3, where M = W and Mo; X = neopentyl, tert-butoxide, and dimethyl amide) and their reactivities toward catalytic olefin metathesis. Dynamic nuclear polarization (DNP)-enhanced solid-state nuclear magnetic resonance (SSNMR), diffuse reflectance infrared Fourier transform (DRIFT), UV resonance Raman, and X-ray absorption (XAS) spectroscopies suggest that upon heterogenization the dimers bind to the surface in a monopodal fashion, with the M≡M triple bond remaining intact. These structural assignments were further corroborated by density functional theory (DFT) calculations. While the homogeneous dimer counterparts are inert, the supported low-valent alkyl W and Mo dimers become active for the disproportionative self-metathesis of propylene to ethylene and butenes and 4-nonene to 4-octene and 5-decene under mild conditions. The lack of activity observed for the free and supported tert-butoxide and dimethyl amide dimers likely suggests that the neopentyl groups are necessary for the formation of a putative alkylidene active species. The difference in reactivity between the free and supported dimers could be explained either by the lowering of the activation barrier of the complex through the electronic effects of the surface or by site isolation of catalytically relevant reactive intermediates.

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Research Organization:: Energy Frontier Research Centers (EFRC) (United States). Energy Frontier Research Center for Inorganometallic Catalyst Design (ICDC); Argonne National Lab. (ANL), Argonne, IL (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division; USDOE Office of Energy Efficiency and Renewable Energy (EERE), Transportation Office. Vehicle Technologies Office

Grant/Contract Number:: AC02-06CH11357; AC02-07CH11358; SC0012702; FG02-03ER15457

OSTI ID:: 1632171

Journal Information:: Organometallics, Vol. 39, Issue 7; ISSN 0276-7333

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 8 works

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Group VI dimers
Olefin metathesis
alkylidene
bimetallic
propylene

CCDC 1968533: Experimental Crystal Structure Determination Alon, Chapovetsky,; R., Langeslay, Ryan; Gokhan, Celik, https://doi.org/10.5517/ccdc.csd.cc242f2r The current record is supplemented by this dataset	dataset	January 2020
CCDC 1968534: Experimental Crystal Structure Determination Alon, Chapovetsky,; R., Langeslay, Ryan; Gokhan, Celik, https://doi.org/10.5517/ccdc.csd.cc242f3s The current record is supplemented by this dataset	dataset	January 2020

Title: Activation of Low-Valent, Multiply M–M Bonded Group VI Dimers toward Catalytic Olefin Metathesis via Surface Organometallic Chemistry

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