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Copper-Catalyzed Oxidative Cleavage of the C–C Bonds of β-Alkoxy Alcohols and β-1 Compounds

[Image: see text] Copper-catalyzed aerobic oxidation conditions were employed to promote the C–C bond cleavage of β-alkoxy alcohols and β-1 compounds (lignin model compounds). Besides these compounds, various 1,2 and 1,3-diols were successfully converted to aldehydes. We propose the Cu(I)-catalyzed...

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Autores principales: Kim, Si Ae, Kim, Seong Eon, Kim, Yu Kwon, Jang, Hye-Young
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7745431/
https://www.ncbi.nlm.nih.gov/pubmed/33344820
http://dx.doi.org/10.1021/acsomega.0c04162
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author Kim, Si Ae
Kim, Seong Eon
Kim, Yu Kwon
Jang, Hye-Young
author_facet Kim, Si Ae
Kim, Seong Eon
Kim, Yu Kwon
Jang, Hye-Young
author_sort Kim, Si Ae
collection PubMed
description [Image: see text] Copper-catalyzed aerobic oxidation conditions were employed to promote the C–C bond cleavage of β-alkoxy alcohols and β-1 compounds (lignin model compounds). Besides these compounds, various 1,2 and 1,3-diols were successfully converted to aldehydes. We propose the Cu(I)-catalyzed mechanism explaining the C–C cleavage of these 1,2 and 1,3-dihydroxy compounds and β-alkoxy alcohols based on XPS data. Although our reaction conditions do not include large excess of bases and elaborated ligand-modified catalysts, copper salts with/without Me-TBD show good catalytic activities for C–C bond cleavage of various lignin model compounds.
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spelling pubmed-77454312020-12-18 Copper-Catalyzed Oxidative Cleavage of the C–C Bonds of β-Alkoxy Alcohols and β-1 Compounds Kim, Si Ae Kim, Seong Eon Kim, Yu Kwon Jang, Hye-Young ACS Omega [Image: see text] Copper-catalyzed aerobic oxidation conditions were employed to promote the C–C bond cleavage of β-alkoxy alcohols and β-1 compounds (lignin model compounds). Besides these compounds, various 1,2 and 1,3-diols were successfully converted to aldehydes. We propose the Cu(I)-catalyzed mechanism explaining the C–C cleavage of these 1,2 and 1,3-dihydroxy compounds and β-alkoxy alcohols based on XPS data. Although our reaction conditions do not include large excess of bases and elaborated ligand-modified catalysts, copper salts with/without Me-TBD show good catalytic activities for C–C bond cleavage of various lignin model compounds. American Chemical Society 2020-12-02 /pmc/articles/PMC7745431/ /pubmed/33344820 http://dx.doi.org/10.1021/acsomega.0c04162 Text en © 2020 American Chemical Society This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes.
spellingShingle Kim, Si Ae
Kim, Seong Eon
Kim, Yu Kwon
Jang, Hye-Young
Copper-Catalyzed Oxidative Cleavage of the C–C Bonds of β-Alkoxy Alcohols and β-1 Compounds
title Copper-Catalyzed Oxidative Cleavage of the C–C Bonds of β-Alkoxy Alcohols and β-1 Compounds
title_full Copper-Catalyzed Oxidative Cleavage of the C–C Bonds of β-Alkoxy Alcohols and β-1 Compounds
title_fullStr Copper-Catalyzed Oxidative Cleavage of the C–C Bonds of β-Alkoxy Alcohols and β-1 Compounds
title_full_unstemmed Copper-Catalyzed Oxidative Cleavage of the C–C Bonds of β-Alkoxy Alcohols and β-1 Compounds
title_short Copper-Catalyzed Oxidative Cleavage of the C–C Bonds of β-Alkoxy Alcohols and β-1 Compounds
title_sort copper-catalyzed oxidative cleavage of the c–c bonds of β-alkoxy alcohols and β-1 compounds
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7745431/
https://www.ncbi.nlm.nih.gov/pubmed/33344820
http://dx.doi.org/10.1021/acsomega.0c04162
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