Catalyst-free decarboxylative cross-coupling of N-hydroxyphthalimide esters with tert-butyl 2-(trifluoromethyl)acrylate and its application

Here, we demonstrate a practical method toward the facile synthesis of CF3-containing amino acids through visible light promoted decarboxylative cross-coupling of a redox-active ester with tert-butyl 2-(trifluoromethyl)acrylate. The reaction was driven by the photochemical activity of electron donor...

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Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 22; no. 11; pp. 2279 - 2283
Main Authors Li, Rui, Yin, Susu, Xie, Lang, Li, Xuefei, Jia, Jia, Zhao, Liang, He, Chun-Yang
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 13.03.2024
Royal Society of Chemistry
Subjects
Amino acids
Catalysts
Chemistry
Chemistry, Organic
Cross coupling
Esters
Functional groups
Photochemicals
Physical Sciences
Science & Technology
BEPOTASTINE
DESIGN
ASYMMETRIC-SYNTHESIS
PEPTIDES
PREGABALIN
PI INTERACTIONS
AMINO-ACID-RESIDUES
FLUORINE
PERFLUOROALKYLATION
DISCOVERY
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Summary:Here, we demonstrate a practical method toward the facile synthesis of CF3-containing amino acids through visible light promoted decarboxylative cross-coupling of a redox-active ester with tert-butyl 2-(trifluoromethyl)acrylate. The reaction was driven by the photochemical activity of electron donor-acceptor (EDA) complexes that were formed by the non-covalent interaction between a Hantzsch ester and a redox-active ester. The advantages of this protocol are its synthetic simplicity, rich functional group tolerance, and a cost-effective reaction system.
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ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob02103c