Categories: C-C Bond Formation > Heteroatom-containing Molecules > Trifluoromethylation
Synthesis of β-trifluoromethyl amines
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Recent Literature
The use of TFSP, a readily available trifluoromethylation reagent prepared from DMAP and Tf2O, enables a general method for the hydrotrifluoromethylation
of styrenes under photoredox catalysis without polymerization. The substrate
scope was further extended to unactivated alkenes, acrylates, acrylamides, and
vinyl-heteroatom-substituted alkenes.
Y.-F. Yang, J.-H. Lin, J.-C. Xiao, Org. Lett., 2021, 23,
9277-9282.
Intermolecular aminotrifluoromethylation of alkenes catalyzed by [Ru(bpy)3]2+
under visible light irradiation achieves highly efficient and regioselective
difunctionalization of C═C bonds, leading to various β-trifluoromethylamines.
The reaction is also applied to "late-stage aminotrifluoromethylation" of
steroid and amino acid scaffolds.
Y. Yasu, T. Koike, M. Akita, Org. Lett., 2013,
15, 2136-2139.
The use of a trifluoromethylsulfonylpyridinium salt (TFSP), easily obtained
by a one-step reaction of Tf2O with 4-dimethylaminopyridine, enables
a trifluoromethylative difunctionalization of alkenes by photoredox catalysis.
DMSO and CH3CN are suitable solvents for achieving keto- and
amino-trifluoromethylation of alkenes, respectively, with good functional group
tolerance.
Z. Wang, J.-H. Lin, J.-C. Xiao, Org. Lett., 2024,
26,
1980-1984.
Related
A mild and efficient DBN-mediated addition of α-(trifluoromethyl)styrenes to
diazoles, triazoles, tetrazoles, and primary, secondary, and secondary cyclic
amines provides various β-trifluoromethyl nitrogen-containing heterocycles and
β-trifluoromethyl amines.
J. He, C. Liu, Y. Deng, Q. Zeng, Y. Zhang, Y. Liu, P. Zheng, S. Cao, Org. Lett.,
2022, 24, 2299-2304.