Categories: C-C Bond Formation > Heteroatom-containing Molecules > Trifluoromethylation
Synthesis of β-trifluoromethyl alcohols
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Recent Literature
Various tertiary β-trifluoromethyl alcohols can be synthesized in good yields
without transition metal catalysts via a radical trifluoromethylation of alkenes
using in situ generated peroxide in NMP under O2 as the radical
initiator.
C. Liu, Q. Lu, Z. Huang, J. Zhang, F. Liao, P. Peng, A. Lei, Org. Lett.,
2015,
17, 6034-6037.
A green, oxidant-free electrochemical method enables radical bromination,
chlorination and trifluoromethylation-formyloxylation of various alkenes with
readily available halogen radical (NaCl, NaBr), and trifluoromethyl radical (CF3SO2Na)
sources in DMF as formyloxylation reagent in an undivided electrochemical cell.
X. Sun, H.-X. Ma, T.-S. Mei, P. Fang, Y. Hu,
Org. Lett., 2019, 21, 3167-3171.
Related
An organocatalytic α-trifluoromethylation and α-perfluoroalkylation of aldehydes
with commercially available perfluoroalkyl halides in the presence of a readily
available iridium photocatalyst and a chiral imidazolidinone catalyst delivers
products with high efficiency and enantioselectivity. α-Trifluoromethyl
aldehydes are versatile precursors for the construction of enantioenriched
trifluoromethylated building blocks.
D. A. Nagib, M. E. Scott, D. W. C. MacMillan, J. Am. Chem. Soc., 2009,
131, 10875-10877.
A nickel-catalyzed asymmetric reductive cross-coupling trifluoroalkylation of
acyl chlorides enables an enantioselective synthesis α-trifluoromethylated
ketones. A one-pot reduction furnished alcohols bearing β-CF3-substituted
stereogenic carbons with excellent diastereoselectivity. The reactions offer
high yields/enantioselectivity, mild conditions, and good functional group
compatibility.
B.-B. Wu, J. Xu, K.-J. Bian, Q. Gao, X.-S. Wang, J. Am. Chem. Soc.,
2022, 144, 6543-6550.
A constant current electrolysis synergizing with a Lewis-acid catalysis
protocol enables an external oxidant-free oxytrifluoromethylation and
aminotrifluoromethylation of styrene derivatives using sodium
trifluoromethanesulfinate as the trifluoromethyl source.
L. Zhang, G. Zhang, P. Wang, Y. Li, A. Lei, Org. Lett.,
2018, 20, 7396-7399.