An efficient method for C()-CHF bond formation was successfully developed by copper-catalyzed cross-coupling of allyl phosphate with 2-fluoro-2-(trimethylsilyl)acetate. Under moderate circumstances, the conversion was carried out in a good strategic range to provide a series of monofluoroalkylation products in high yields, which also demonstrates the practicality of gram-scale reactions.
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http://dx.doi.org/10.1021/acs.joc.3c00064 | DOI Listing |
Chem Commun (Camb)
April 2024
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai, 200032, China.
The unprecedented copper-catalyzed asymmetric alkynylallylic monofluoroalkylation reaction is described the use of 1,3-enynes and fluorinated malonates. A series of 1,4-enynes bearing a monofluoroalkyl unit are achieved in high yields, excellent regio- and enantioselectivity and high selectivity. The asymmetric propargylic monofluoroalkylation is also developed.
View Article and Find Full Text PDFOrg Lett
June 2023
Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, China.
A photoinduced copper-catalyzed strategy for the monofluoroalkylation of alkynes with readily available monofluoroalkyl triflates was developed. It provides a new protocol to access valuable propargyl fluoride compounds via C-C bond formation by avoiding the use of highly toxic fluorination reagents. This reaction proceeded under mild conditions to afford propargyl monofluorides in moderate to high yields.
View Article and Find Full Text PDFJ Org Chem
June 2023
School of Chemistry and Chemical Engineering, Hefei University of Technology, 193 Tunxi Road, Anhui 230009, China.
An efficient method for C()-CHF bond formation was successfully developed by copper-catalyzed cross-coupling of allyl phosphate with 2-fluoro-2-(trimethylsilyl)acetate. Under moderate circumstances, the conversion was carried out in a good strategic range to provide a series of monofluoroalkylation products in high yields, which also demonstrates the practicality of gram-scale reactions.
View Article and Find Full Text PDFOrg Biomol Chem
April 2023
School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, China.
A novel copper-catalyzed three-component reaction of monofluoroalkylation agents, alkenes and TMSCN is described. In addition, alkynes could also be compatible with the reaction system to obtain three-component products for the first time with moderate yield and excellent / stereoselectivity. This reaction provides a facile method for the synthesis of cyanomonofluoroalkyl compounds, which may serve as potentially useful organic intermediates for further transformations.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
September 2022
Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui, 230026, China.
Monofluoroalkanes are important in many pharmaceuticals, agrochemicals and functional materials. However, the lack of easily available and transformable monofluoroalkylating reagents that facilitate a broad array of transformations has hampered the application of monofluoroalkylation. Herein, we report a general and efficient method of preparing diverse aliphatic monofluorides with monofluoroalkyl triflate as the synthetic scaffold.
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