Synthesis of α,β‐Unsaturated Ketones with Secondary Alcohols and Aldehydes Catalyzed by Fe(acac)3

An efficient and environmentally friendly methodology for the direct synthesis of α,β‐unsaturated ketones by cross‐coupling of secondary alcohols and aldehydes is developed. The transformation is based on Fe(acac)3‐catalyzed Oppenauer oxidation and Claisen‐Schmidt reaction, in which aldehydes are us...

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Bibliographic Details
Published in:ChemistrySelect (Weinheim) 2022-09, Vol.7 (34), p.n/a
Main Authors: Zhao, Zhengjia, Yu, Xiangzhu, Zhu, Lina, Tan, Shangzhi, Fu, Weiru, Wang, Lianyue, An, Yue
Format: Article
Language:English
Subjects:
base-free
Fe(acac)3
Oppenauer oxidation
secondary alcohols
α,β-unsaturated ketones
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Summary:An efficient and environmentally friendly methodology for the direct synthesis of α,β‐unsaturated ketones by cross‐coupling of secondary alcohols and aldehydes is developed. The transformation is based on Fe(acac)3‐catalyzed Oppenauer oxidation and Claisen‐Schmidt reaction, in which aldehydes are used as oxidants to oxidize secondary alcohols to ketones, and then in situ condensation with aldehydes to form α,β‐unsaturated ketones. The reaction proceeds under base‐free conditions with a wide range of substrates and good compatibility of functional groups. Gram‐scale experiments show the good applicability of this method. Direct synthesis of α,β‐unsaturated ketones by cross‐coupling of secondary alcohols and aldehydes catalyzed by Fe(acac)3 is described. The reaction proceeds under base‐and ligand‐free conditions with a wide range of substrates and good compatibility of functional groups.
ISSN:2365-6549
2365-6549
DOI:10.1002/slct.202202093