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Ru(dppbsa)-catalyzed hydrodeoxygenation and reductive etherification of ketones and aldehydes
Sun, Rui1,2; Hon-Yu Guo1,3; Shuang-Shuang Ma1,2; Yao-Feng Wang1; Zheng-Kun Yu4; Bao-Hua Xu1,2,4
2022-02-14
Source PublicationORGANIC CHEMISTRY FRONTIERS
ISSN2052-4129
Pages12
AbstractMethods for the Ru(dppbsa)-catalyzed hydrodeoxygenation and reductive etherification of ketones and aldehydes were developed. Carbonyl substrates without beta-CH functionality follow a hydrogenation-hydrogenolysis path, wherein the hydrogenolysis of the alkanol intermediates is the rate-limiting step. By contrast, a hydrogenation-dehydration-hydrogenation path is followed by carbonyl substrates with beta-CH functionality, suffering from rate-limiting sulfonate ligand-assisted reversible H-2 cleavage. This hydrodeoxygenation is competitive with reductive etherification when using alkanols as hydrogen surrogates. The chemoselectivity can be adjusted based not only on the bond strengths of O-H and C-H bonds in the alkanols but also on the steric hindrance of the carbonyl substrates. As a result, both hydrodeoxygenation and reductive etherification exhibit excellent aldehyde tolerance, while the reductive etherification of ketones is highly hindered based on this protocol.
DOI10.1039/d1qo01717a
Language英语
WOS KeywordH BOND ACTIVATION ; CARBOXYLIC-ACIDS ; DEOXYGENATIVE HYDROGENATION ; CATALYZED HYDROGENATION ; CARBONYL-COMPOUNDS ; BRONSTED ACIDITY ; AMIDES ; ALCOHOLS ; LEWIS ; MILD
Funding ProjectExcellent Young Scientists Fund[22022815] ; Innovation Academy for Green Manufacture, CAS[IAGM2020C13] ; Zhengzhou High Level Talent Certificate[20180200052] ; K. C. Wong Education Foundation[GJTD-2018-04]
WOS Research AreaChemistry
WOS SubjectChemistry, Organic
Funding OrganizationExcellent Young Scientists Fund ; Innovation Academy for Green Manufacture, CAS ; Zhengzhou High Level Talent Certificate ; K. C. Wong Education Foundation
WOS IDWOS:000760909800001
PublisherROYAL SOC CHEMISTRY
Citation statistics
Document Type期刊论文
Identifierhttp://ir.ipe.ac.cn/handle/122111/52126
Collection中国科学院过程工程研究所
Corresponding AuthorBao-Hua Xu
Affiliation1.Chinese Acad Sci, CAS Key Lab Green Proc & Engn Inst Proc Engn, Beijing Key Lab Ion Liquids Clean Proc, Beijing 100190, Peoples R China
2.Univ Chinese Acad Sci, Coll Chem & Chem Engn, Beijing 100049, Peoples R China
3.Hefei Univ, Dept Biol & Environm Engn, Hefei 230601, Anhui, Peoples R China
4.Chinese Acad Sci, Innovat Acad Green Manufacture, Beijing 100190, Peoples R China
Recommended Citation
GB/T 7714
Sun, Rui,Hon-Yu Guo,Shuang-Shuang Ma,et al. Ru(dppbsa)-catalyzed hydrodeoxygenation and reductive etherification of ketones and aldehydes[J]. ORGANIC CHEMISTRY FRONTIERS,2022:12.
APA Sun, Rui,Hon-Yu Guo,Shuang-Shuang Ma,Yao-Feng Wang,Zheng-Kun Yu,&Bao-Hua Xu.(2022).Ru(dppbsa)-catalyzed hydrodeoxygenation and reductive etherification of ketones and aldehydes.ORGANIC CHEMISTRY FRONTIERS,12.
MLA Sun, Rui,et al."Ru(dppbsa)-catalyzed hydrodeoxygenation and reductive etherification of ketones and aldehydes".ORGANIC CHEMISTRY FRONTIERS (2022):12.
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