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Issue 26, 2019
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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

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Abstract

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.

Graphical abstract: 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

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Publication details

The article was received on 26 Dec 2018, accepted on 08 Feb 2019 and first published on 09 Feb 2019


Article type: Communication
DOI: 10.1039/C8CC10212K
Citation: Chem. Commun., 2019,55, 3705-3708

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    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

    Y. Lou, A. Wang, L. Zhao, L. He, X. Li, C. He and X. Zhang, Chem. Commun., 2019, 55, 3705
    DOI: 10.1039/C8CC10212K

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