Recent advances in the synthesis of trifluoromethyl-containing heterocyclic compounds via trifluoromethyl building blocks

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(31), P. 6246 - 6276

Published: Jan. 1, 2024

Recent advances in the preparation of trifluoromethyl-containing heterocyclics via trifluoromethyl building block strategies over period from 2019 to present are systematically summarized and discussed.

Language: Английский

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Copper-Mediated Cyclization of Terminal Alkynes with CF₃-Imidoyl Sulfoxonium Ylides To Construct 5-Trifluoromethylpyrroles

Organic Letters, Journal Year: 2024, Volume and Issue: 26(11), P. 2249 - 2254

Published: March 7, 2024

A copper-mediated [3 + 2] cyclization of CF3-imidoyl sulfoxonium ylides and terminal alkynes has been demonstrated. This work provides a practical approach for assembling 5-trifluoromethylpyrroles with the merits broad substrate scope, good functional tolerance, mild reaction conditions. Control experiments DFT studies indicate that this may involve addition π-bonds by copper-carbene radicals hydrogen migration.

Language: Английский

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Trifluoromethyl Group (CF₃) Induced Regioselective Larock Indole Synthesis from Unsymmetric β-CF₃-1,3-enynes

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 24, 2025

The indole skeleton exists widely in natural products, pharmaceuticals, and materials. We disclose here a trifluoromethyl group induced regioselective Larock synthetic method from unsymmetric 2-CF3-1,3-enynes. presence of is determinable for the regioselectivity. Once CF3 was replaced with methyl or phenyl group, ratio 1:1 to 1:1.4 isomers were obtained. This strategy features good regioselectivity, broad substrate scope, high functional tolerance. protocol reported offers an alternative solution rare 3,4-functionalization products further transformed show distinctive reactivity hydroboration–oxidation hydro-bromination.

Language: Английский

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Recent advancement on metal free hydroamination reaction of C-C multiple bonds.

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134625 - 134625

Published: March 1, 2025

Language: Английский

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Transition Metal-Free Domino Hydroamination/Isomerization/Transamidation Sequence: An Entry to Trifluorinated γ-Lactams

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10644 - 10653

Published: July 16, 2024

A method for the construction of trifluorinated-5-methylenepyrrolidinone is reported. This strategy combines an acid-catalyzed two-carbon homologation process between ynamides and aldehydes, providing CF

Language: Английский

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γ-CF₃-Allenamides versus 3-CF₃-Cyclopentenylamines: Substituent-Controlled Divergent Reaction of β-CF₃-1,3-Enynamides with β-Dicarbonyl Compounds

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13789 - 13794

Published: Sept. 10, 2024

A distinctive

Language: Английский

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Regioselective Intermolecular Hydroamidation of β‐CF3‐1,3‐enynamides: An Approach to Tri‐substituted γ‐CF3‐allenamides

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(44)

Published: Oct. 14, 2024

Abstract A simple base mediated, highly regioselective 1,4‐hydroamidation of β ‐CF 3 ‐1,3‐enynamides with secondary amides for synthesis tri‐substituted γ ‐allenamides compounds was developed. N ‐alkyl sulfonamides are generally good candidates the present transformation. could be employed potential value‐added such as fluorinated halogenated pyrrole, tetrahydroquinoline and 2‐CF ‐putrescine derivatives.

Language: Английский

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