Categories: C-C Bond Formation > Heteroatom-containing Molecules, Chains > Trifluoromethylation
Synthesis of trifluoromethyl alkynes
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Recent Literature
A fluoroform-derived CuCF3 reagent can be prepared in large
quantities and is convenient to use. This reagent, prepared from inexpensive
industrial waste fluoroform (CF3H), enables an efficient
trifluoromethylation reaction of alkynes in presence of the diamine ligand
tetramethylethylenediamine (TMEDA).
L. He, G. C. Tsui, Org. Lett.,
2016, 18, 2800-2803.
The nucleophilic trifluoromethylating reagent Me3SiCF3
enables an efficient copper-mediated trifluoromethylation of terminal alkynes.
Various functionalities were tolerated under the reaction conditions. This
reaction provides a general, straightforward, and practically useful method to
prepare trifluoromethylated acetylenes.
L. Chu, F.-L. Qing, J. Am. Chem. Soc., 2010,
132, 7262-7263.
An efficient copper-catalyzed oxidative trifluoromethylation of terminal alkynes
and aryl boronic acids in the presence of air is successfully achieved by adding
both the substrate and a portion of CF3TMS slowly using a syringe
pump to the reaction mixture.
X. Jiang, L. Chu, F.-L. Qing, J. Org. Chem., 2012,
77, 1251-1257.
An organic photocatalyst mediates a deconstructive alkynylation of an
unstrained ketone under blue light irradiation. This alkynylation method offers
a broad substrate scope and excellent functional group tolerance. A
trifluoromethylation reagent for the trifluoromethylation reaction of various
alkynyl bromides is also described.
H. Wu, S. Chen, D. Xiao, F. Li, K. Zhou, X. Yin, C. Liu, X. He, Y. Shang, Org. Lett., 2023, 25,
1166-1171.