AgF/TFA-promoted highly efficient synthesis of α-haloketones from haloalkynes
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A AgF/TFA-promoted highly efficient synthesis of a wide range of α-haloketones from haloalkynes is described. The reactions are conducted under convenient conditions and provide products in moderate to excellent yields, with broad substrate scope, including a variety of aromatic chloroalkynes and bromoalkynes.
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Acknowledgements
The authors thank the NSFC (21202023 and 21162001), NSF of Jiangxi Province (20114BAB213006) for financial support.
References and notes (23)
- et al.
Tetrahedron Lett.
(1999) - et al.
J. Org. Chem.
(1963) - et al.
J. Org. Chem.
(2009)et al.Synth. Commun.
(2006)et al.Synth. Commun.
(2006)et al.Bull. Korean Chem. Soc.
(1995)et al.Synthesis
(1982) - et al.
Molecules
(2003) - et al.
- et al.
Org. Synth. Coll. III
(1955) - et al.
J. Org. Chem.
(1964) - et al.
Bull. Korean Chem. Soc.
(2003)et al.Tetrahedron Lett.
(2011)et al.Tetrahedron
(2008) - et al.
J. Org. Chem.
(1989)et al.J. Org. Chem.
(1995)et al.Org. Lett.
(2006)et al.Org. Lett.
(2003)et al.J. Am. Chem. Soc.
(1950)
J. Org. Chem.
J. Org. Chem.
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