Categories: C-C Bond Formation > Heteroatom-containing Molecules > Trifluoromethylation
Synthesis of α-trifluoromethyl amines
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Recent Literature
TMSCF3 and tetrabutylammonium (triphenylsilyl) difluorosilicate (TBAT)
were used for efficient nucleophilic trifluoromethylation of aromatic, aliphatic
and α,β-unsaturated sulfonaldimines to yield the corresponding sulfonamide
adducts in good to excellent yields.
G. K. S. Prakash, M. Mandal, G. A. Olah,
Synlett, 2001, 77-78.
A nucleophilic trifluoromethylation reaction of carbonyl
compounds with Ruppert’s reagent, Me3SiCF3, was efficiently
promoted by a P(t-Bu)3-DMF system. Imines were also converted to the desired
α-trifluoromethyl amines under similar reaction conditions.
S. Mizuta, N. Shibata, T. Sato, H. Fujimoto, S. Nakamura, T. Toru, Synlett,
2006, 267-270.>
Alkoxide-induced nucleophilic pentafluoroethylation and trifluoromethylation
of aldehydes, ketones, and imines using pentafluoroethyl phenyl sulfone and
trifluoromethyl phenyl sulfone, respectively, have been successfully achieved.
G. K. S. Prakash, Y. Wang, R. Mogi, J. Hu, T. Mathew, G. A. Olah, Org. Lett., 2010,
12, 2932-2935.
An iridium photocatalyst enables the addition of fluorinated groups to nitrones
using ascorbic acid as a stoichiometric reducing agent. Partially fluorinated
alkyl iodides can also be effectively used. The resulting hydroxylamines can be
readily converted to valuable fluorinated amines by reduction with zinc.
V. I. Supranovich, V. V. Levin, M. I. Struchkova, A. D. Dilman, Org. Lett.,
2018, 20, 840-843.
Related
A chiral pyridoxamine catalyzes an asymmetric biomimetic transamination of
trifluoromethyl ketones with 2,2-diphenylglycine as the amine source to produce
optically active α-trifluoromethyl amines in very good yields with excellent
ee's under mild conditions.
W. Cai, D. Cai, H. Liang, X. Ren, B. Zhao, J. Org. Chem., 2023, 88,
7849-7857.
A BINOL-derived boro-phosphate catalyzes an enantioselective reduction of
α-trifluoromethylated imines to provide chiral α-trifluoromethylated amines in
high yields and with excellent enantioselectivities in the presence of
catecholborane as hydride source under mild conditions.
H. He, X. Tang, Y. Cao, J. C. Antilla, J. Org. Chem., 2021, 86,
4336-4345.
The use of a commercially available Umemoto’s reagent enables a metal-free
trifluoromethylation of nitroalkanes. This method provides quaternary
α-(trifluoromethyl)nitroalkanes, that can be elaborated to various complex
nitrogen-containing molecules, including α-(trifluoromethyl)amines.
A. S. Gietter-Burch, V. Devannah, D. A. Watson, Org. Lett.,
2017, 19, 2957-2960.