Trifluoroacetylation in Organic Synthesis: Reagents, Developments and Applications in the Construction of Trifluoromethylated Compounds

López, Simón E.; Restrepo, Jelem; Salazar, José A.

doi:10.2174/157017910792246126

Cited by 26 publications

(16 citation statements)

References 86 publications

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“…Finally, further applications of this method were demonstrated (Scheme ). The trifluoroacetyl group of 8 can be easily deprotected under mildly acidic conditions, providing α‐aminoketone hydrochloride 14 , a key intermediate for various heterocycles,, in high yield. Oxazole 15 was synthesized from 14 by simple oxidative coupling with an aldehyde (Scheme a).…”

Section: Methodsmentioning

confidence: 99%

Photoactivated N‐Acyliminoiodinanes Applied to Amination: an ortho‐Methoxymethyl Group Stabilizes Reactive Precursors

2017

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N-Acyliminoiodinanes were characterized for the first time by X-ray structural analysis. The ortho-methoxymethyl group and the carbonyl oxygen coordinate to the iodine atom of the iminoiodinane. Activation of the N-acyliminoiodinane was achieved by photoirradiation at 370 nm, thereby enabling reaction with various silyl enol ethers to give α-aminoketone derivatives in good to high yield. N-sulfonyliminoiodinanes bearing ortho substituents were used in photoinduced amination.

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Section: Methodsmentioning

confidence: 99%

Photoactivated N‐Acyliminoiodinanes Applied to Amination: an ortho‐Methoxymethyl Group Stabilizes Reactive Precursors

2017

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Section: Methodsmentioning

confidence: 99%

“…The trifluoroacetate ester itself can be installed as a non-enolisable acetyl protecting group for alcohols, amines and thiols. 4 It is typically introduced by the condensation of trifluoroacetic anhydride (TFAA) or ethyl trifluoroacetate and removed by base hydrolysis or transesterification. A high level of acidity and solubility in both organic and aqueous solvents makes TFA an ideal reagent to activate polarised functional groups and promote the generation of organic cations in solution, which can encourage cyclisation reactions, rearrangements and multi-bond forming processes.…”

Section: Introductionmentioning

confidence: 99%

Trifluoroacetic Acid (TFA)

Norris¹

2015

Synlett

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was born in Bedford Park, South Australia and studied organic chemistry at Flinders University, receiving his B.Sc. (Hons) in 2011. He was then awarded the MF & MH Joyner Scholarship in Science and began doctoral work as a student of Associate Professor Michael V. Perkins. Matthew also received the Australian Fulbright Alumni (WG Walker) Postgraduate Scholarship and worked with Professor Erik J. Sorensen at Princeton University in 2014. His research has focused on chemical synthesis and methodology with a strong emphasis on the total synthesis of natural products.

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“…The preparation and application of 1,1,1-trifluoro-4-alkoxy-3alken-2-ones are presently well documented [1,2]. In the last two decades, β-alkoxy-α,β-unsaturated trifluoromethyl ketones [as 1,1,1-trifluoro-4-alkoxy-3-alken-2-ones (a), 1-methoxy-2trifluoroacetylcycloalk-1-enes (b), 3-trifluoroacetyl-4,5-dihydrofuran (c), and 3-trifluoroacetyl-5,6-dihydro-4H-pyran (d) ( Figure 1)], which are formally trifluoroacetylated enol ethers, have proved to be important building blocks for hetero-and carbocyclic compounds [1][2][3]. In view of the importance of heterocyclic thiophene systems, we have focused our attention on the synthesis of thien-2-yl-substituted dielectrophiles [4].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Structure, and Cyclocondensation of the 4,4,4-Trifluoro-3,3-dihydroxy-2-methyl-1-(thien-2-yl)-1-butanone with Hydroxylamine and Hydrazine

Flores

Kuhn

Flores

et al. 2018

Journal of Spectroscopy

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The synthesis of 4,4,4-trifluoro-3,3-dihydroxy-2-methyl-1-(thien-2-yl)butan-1-one (3) through acylation of 1,1-dimethoxy-1-(thien-2-yl)propane (1) with trifluoroacetic anhydride and its reactions with hydroxylamine and hydrazine was investigated. X-ray structural analysis of new trifluoromethyl-substituted dielectrophile 3 revealed that this hydrate exists as a racemate with inter- and intramolecular O-H·O bonds. The crystal structure shows alignment along axis b of pair molecules with the same configuration of the O2-H·O1 bond. For 5(3)-trifluoromethyl-4-methyl-3(5)-(thien-2-yl)-1H-pyrazole (4), obtained via cyclocondensation of precursor 2 and hydrazine hydrochloride, X-ray structural analysis indicated that its rings are almost planar (torsion angle N2-C5-C6-C7–5.4°) and that S1 at the thienyl moiety is anti-periplanar to N2 (torsion angle N2-C5-C6-S1 176.01); no disorder effect was observed for the thienyl ring.

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Trifluoroacetylation in Organic Synthesis: Reagents, Developments and Applications in the Construction of Trifluoromethylated Compounds

Cited by 26 publications

References 86 publications

Photoactivated N‐Acyliminoiodinanes Applied to Amination: an ortho‐Methoxymethyl Group Stabilizes Reactive Precursors

Photoactivated N‐Acyliminoiodinanes Applied to Amination: an ortho‐Methoxymethyl Group Stabilizes Reactive Precursors

Trifluoroacetic Acid (TFA)

Synthesis, Structure, and Cyclocondensation of the 4,4,4-Trifluoro-3,3-dihydroxy-2-methyl-1-(thien-2-yl)-1-butanone with Hydroxylamine and Hydrazine

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