Benzimidazoles as Metal-Free and Recyclable Hydrides for CO2 Reduction to Formate

Lim, Chern-Hooi; Ilic, Stefan; Alherz, Abdulaziz; Worrell, Brady T.; Bacon, Samuel S.; Hynes, James T.; Glusac, Ksenija D.; Musgrave, Charles B.

doi:10.1021/jacs.8b09653

Title: Benzimidazoles as Metal-Free and Recyclable Hydrides for CO₂ Reduction to Formate

Journal Article · 26 November 2018 · Journal of the American Chemical Society

DOI: https://doi.org/10.1021/jacs.8b09653 · OSTI ID:1558602

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^[1]; Worrell, Brady T. ^[1]; Bacon, Samuel S. ^[1];

^[3]; Glusac, Ksenija D. ^[2];

^[4]

Univ. of Colorado, Boulder, CO (United States)
Univ. of Illinois, Chicago, IL (United States); Argonne National Lab. (ANL), Argonne, IL (United States)
Univ. of Colorado, Boulder, CO (United States); Pasteur Inst., Paris (France)
Univ. of Colorado, Boulder, CO (United States); National Renewable Energy Lab. (NREL), Golden, CO (United States)

We report a novel metal-free chemical reduction of CO₂ by a recyclable benzimidazole-based organo-hydride, whose choice was guided by quantum chemical calculations. Notably, benzimidazole-based hydride donors rival the hydride-donating abilities of noble-metal-based hydrides such as [Ru(tpy)(bpy)H]⁺ and [Pt(depe)₂H]⁺. Chemical CO₂ reduction to the formate anion (HCOO–) was carried out in the absence of biological enzymes, a sacrificial Lewis acid, or a base to activate the substrate or reductant. ¹³CO₂ experiments confirmed the formation of H¹³COO^– by CO₂ reduction with the formate product characterized by 1H NMR and 13C NMR spectroscopy and ESI-MS. The highest formate yield of 66% was obtained in the presence of potassium tetrafluoroborate under mild conditions. The likely role of exogenous salt additives in this reaction is to stabilize and shift the equilibrium toward the ionic products. After CO₂ reduction, the benzimidazole-based hydride donor was quantitatively oxidized to its aromatic benzimidazolium cation, establishing its recyclability. In addition, we electrochemically reduced the benzimidazolium cation to its organo-hydride form in quantitative yield, demonstrating its potential for electrocatalytic CO₂ reduction. These results serve as a proof of concept for the electrocatalytic reduction of CO₂ by sustainable, recyclable, and metal-free organo-hydrides.

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Research Organization:: Argonne National Laboratory (ANL), Argonne, IL (United States)

Sponsoring Organization:: National Science Foundation (NSF); Petroleum Research Fund (PRF); USDOE

Grant/Contract Number:: AC02-06CH11357

OSTI ID:: 1558602

Journal Information:: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 1 Vol. 141; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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