Chemoselective Hydrogenation with Supported Organoplatinum(IV) Catalyst on Zn(II)-Modified Silica

Camacho-Bunquin, Jeffrey; Ferrandon, Magali; Sohn, Hyuntae; Yang, Dali; Liu, Cong; Ignacio-de Leon, Patricia Anne; Perras, Frédéric A.; Pruski, Marek; Stair, Peter C.; Delferro, Massimiliano

doi:10.1021/jacs.7b11981

Chemoselective Hydrogenation with Supported Organoplatinum(IV) Catalyst on Zn(II)-Modified Silica

Journal Article · Mon Feb 26 23:00:00 EST 2018 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.7b11981· OSTI ID:1427735

^[1]; Ferrandon, Magali ^[1]; Sohn, Hyuntae ^[1]; Yang, Dali ^[1]; ^[1]; Ignacio-de Leon, Patricia Anne ^[2]; Perras, Frédéric A. ^[3]; ^[4]; Stair, Peter C. ^[5]; ^[1]

Argonne National Lab. (ANL), Lemont, IL (United States). Chemical Sciences and Engineering Division
Argonne National Lab. (ANL), Lemont, IL (United States). Energy Sciences Division
Ames Lab., Ames, IA (United States)
Ames Lab., Ames, IA (United States); Iowa State Univ., Ames, IA (United States). Department of Chemistry
Argonne National Lab. (ANL), Lemont, IL (United States). Chemical Sciences and Engineering Division ; Northwestern Univ., Evanston, IL (United States). Department of Chemistry

For this research, well-defined organoplatinum(IV) sites were grafted on a Zn(II)-modified SiO₂ support via surface organometallic chemistry in toluene at room temperature. Solid-state spectroscopies including XAS, DRIFTS, DRUV–vis, and solid-state (SS) NMR enhanced by dynamic nuclear polarization (DNP), as well as TPR-H₂ and TEM techniques revealed highly dispersed (methylcyclopentadienyl)methylplatinum(IV) sites on the surface ((MeCp)PtMe/Zn/SiO₂, 1). In addition, computational modeling suggests that the surface reaction of (MeCp)PtMe₃ with Zn(II)-modified SiO₂ support is thermodynamically favorable (ΔG = -12.4 kcal/mol), likely due to the increased acidity of the hydroxyl group, as indicated by NH₃-TPD and DNP-enhanced ¹⁷O{¹H} SSNMR. In situ DRIFTS and XAS hydrogenation experiments reveal the probable formation of a surface Pt(IV)-H upon hydrogenolysis of Pt-Me groups. The heterogenized organoplatinum(IV)-hydride sites catalyze the selective partial hydrogenation of 1,3-butadiene to butenes (up to 95%) and the reduction of nitrobenzene derivatives to anilines (up to 99%) with excellent tolerance of reduction-sensitive functional groups (olefin, carbonyl, nitrile, halogens) under mild reaction conditions.

View Accepted Manuscript (DOE)

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

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22). Chemical Sciences, Geosciences & Biosciences Division

Grant/Contract Number:: AC02-06CH11357; AC02-07CH11358

OSTI ID:: 1427735

Report Number(s):: IS-J--9598

Journal Information:: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 11 Vol. 140; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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