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Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
β-CF3 Alkynones for Amine Conjugation under Aqueous Conditions
Fanyi Hou1, Jinzan Feng1, Teck-Peng Loh1,2
1Henan Linker Technology Key Laboratory, College of Advanced Interdisciplinary Science and Technology (CAIST), Henan University of Technology, Zhengzhou450001, China.
Abstract:
We report an aqueous conjugate addition of primary and secondary amines to β-CF3 alkynones under mild conditions without added metal catalysts or activating reagents. This protocol affords stable, CF3-containing enaminone conjugates in phosphate buffer and is applicable to structurally diverse amine substrates. Its utility is demonstrated by the modification of drugs, amino acid esters, dipeptides, complex bioactive peptides, and proteins, as well as two-step fluorescent labeling of lysozyme confirmed by fluorescence SDS-PAGE analysis.
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