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Categories: C-C Bond Formation > Heteroatom-containing Molecules, Chains > Trifluoromethylation

Synthesis of trifluoromethyl alkynes


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.