Palladium-catalyzed cross-coupling of unactivated alkylzinc reagents with 2-bromo-3,3,3-trifluoropropene and its application in the synthesis of fluorinated amino acids

A palladium-catalyzed cross-coupling of unactivated alkylzinc reagents with 2-bromo-3,3,3-trifluoropropene (BTP) has been developed, which was used as a key step to prepare a series of trifluoromethylated and difluoromethylated amino acids that are of great interest in peptide/protein based chemical...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2019-03, Vol.55 (26), p.3705-3708
Main Authors: Lou, Yue-Guang, Wang, An-Jun, Zhao, Liang, He, Lin-Feng, Li, Xiao-Fei, He, Chun-Yang, Zhang, Xingang
Format: Article
Language:English
Subjects:
Amino acids
Chemical synthesis
Cross coupling
Crystallography
Fluorination
Organic chemistry
Palladium
Proteins
Reagents
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Summary:A palladium-catalyzed cross-coupling of unactivated alkylzinc reagents with 2-bromo-3,3,3-trifluoropropene (BTP) has been developed, which was used as a key step to prepare a series of trifluoromethylated and difluoromethylated amino acids that are of great interest in peptide/protein based chemical biology. The advantages of the synthesis of these fluorinated amino acids are synthetic simplicity and diversity from a simple and readily available key intermediate α-trifluoromethylalkene-containing amino acid, providing a facile route for applications in medicinal chemistry and life science.
ISSN:1359-7345
1364-548X
DOI:10.1039/c8cc10212k