Selective Conversion of Carbon Dioxide to Formaldehyde via a Bis(silyl)acetal: Incorporation of Isotopically Labeled C1 Moieties Derived from Carbon Dioxide into Organic Molecules

Rauch, Michael; Strater, Zack; Parkin, Gerard

doi:10.1021/jacs.9b08342

Title: Selective Conversion of Carbon Dioxide to Formaldehyde via a Bis(silyl)acetal: Incorporation of Isotopically Labeled C₁ Moieties Derived from Carbon Dioxide into Organic Molecules

Journal Article · 22 October 2019 · Journal of the American Chemical Society

DOI: https://doi.org/10.1021/jacs.9b08342 · OSTI ID:1656787

Rauch, Michael ^[1]; Strater, Zack ^[1];

^[1]

Columbia University, New York, NY (United States)

The conversion of carbon dioxide to formaldehyde is a transformation that is of considerable significance in view of the fact that formaldehyde is a widely used chemical, but this conversion is challenging because CO₂ is resistant to chemical transformations. Therefore, we report here that formaldehyde can be readily obtained from CO₂ at room temperature via the bis(silyl)acetal, H₂C(OSiPh₃)₂. Specifically, formaldehyde is released from H₂C(OSiPh₃)₂ upon treatment with CsF at room temperature. H₂C(OSiPh₃)₂ thus serves as a formaldehyde surrogate and provides a means to incorporate CH_x (x = 1 or 2) moieties into organic molecules. Here, isotopologues of H₂C(OSiPh₃)₂ may also be synthesized, thereby providing a convenient means to use CO₂ as a source of isotopic labels in organic molecules.

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Research Organization:: Columbia Univ., New York, NY (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation for a Graduate Research Fellowship

Grant/Contract Number:: SC0019204; FG02-93ER14339; DGE-16-44869

OSTI ID:: 1656787

Journal Information:: Journal of the American Chemical Society, Vol. 141, Issue 44; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Carbon dioxide
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hydrosilylation
isotopologue
redox reactions
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inorganic carbon compounds
organic compounds
aldehydes

Title: Selective Conversion of Carbon Dioxide to Formaldehyde via a Bis(silyl)acetal: Incorporation of Isotopically Labeled C1 Moieties Derived from Carbon Dioxide into Organic Molecules

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