α‑Trifluoromethyl Carbanion-catalyzed Intermolecular Stetter Reaction of Aromatic Aldehydes with 2‑Bromo-3,3,3-trifluoropropene: Synthesis of β‑Alkoxyl-β-trifluoromethylated Ketones

The intermolecular Stetter reaction of aromatic aldehydes with 2-bromo-3,3,3-trifluoropropene is achieved by the in situ generated α-trifluoromethyl carbanion catalyst. It not only represents the first example for α-trifluoromethyl carbanion-catalyzed umpolung reaction but also reveals a new protoco...

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Published inOrganic letters Vol. 24; no. 1; pp. 33 - 37
Main Authors Cai, Yingying, Jiang, Huanfeng, Zhu, Chuanle
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 14.01.2022
Amer Chemical Soc
Subjects
aldehydes
bioactive compounds
catalysts
Chemistry
Chemistry, Organic
hydrogen
ketones
Physical Sciences
Science & Technology
REGIOSELECTIVE SYNTHESIS
FLUORINE
GENERATION
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Summary:The intermolecular Stetter reaction of aromatic aldehydes with 2-bromo-3,3,3-trifluoropropene is achieved by the in situ generated α-trifluoromethyl carbanion catalyst. It not only represents the first example for α-trifluoromethyl carbanion-catalyzed umpolung reaction but also reveals a new protocol for the umpolung of aldehydes. Various useful β-alkoxyl-β-trifluoromethylated ketones were obtained in high yields, which could further convert to attractive bioactive compounds. Mechanism studies indicated an intramolecular 1,4-shift of the hydrogen atom was involved in this reaction.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.1c03553