Silver-Promoted Three-Component Synthesis of Perfluoroalkenyl Pyrroles through Partial Defluorinative Functionalization of Perfluoroalkyl Halides

Organic Letters, Journal Year: 2024, Volume and Issue: 26(29), P. 6197 - 6202

Published: July 15, 2024

A silver-promoted three-component heterocyclization of alkynes, perfluoroalkyl halides, and 1,3-dinucleophiles was developed for the efficient synthesis privileged (E)-perfluoroalkenyl pyrroles. The reaction proceeded through a rationally designed sequence radical perfluoroalkylation intramolecular defluorinative [3 + 2]-heterocyclization. utility halide as perfluoroalkenyl reagent, by selective controllable functionalization two inert C(sp3)–F bonds at vicinal carbon centers on chain, provides new mode value-added organofluorides starting from easily available low-cost fluorinated feedstock.

Language: Английский

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Mild [3 + 3] Annulation of (Trifluoromethyl)alkenes with Thioureas Enabled by Chemoselective Defluorinative Amination: Synthesis of 6-Fluoro-3,4-dihydropyrimidine-2(1H)-thiones

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 90(4), P. 1538 - 1548

Published: Jan. 21, 2025

The chemoselective defluorinative [3 + 3] annulation of (trifluoromethyl)alkenes with thioureas is reported. This protocol affords various attractive 6-fluoro-3,4-dihydropyrimidine-2(1H)-thiones in high yields, features transition-metal free, mild conditions, efficient, operationally simple and gram-scalable, tolerates diverse useful functional groups.

Language: Английский

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Photoinduced Iron-Catalyzed Decarboxylation/Isomerization of gem-Difluoroallyl Carboxylic Acid to Access Vinyl Difluoromethylene Units

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

Published: March 28, 2025

Vinyl difluoromethylene units (−CF−) significantly enhance the bioactivity and physical chemical properties of compounds. Despite recent advances in introducing vinyl units, radical-mediated formation these motifs remains largely unexplored. A novel serial catalytic strategy for selective defluoroalkylation trifluoromethyl alkenes has been developed, utilizing photocatalytic defluorocarboxylation followed by photoinduced iron-catalyzed decarboxylation/isomerization. The reaction involves generating difluoroallyl radicals, tautomerizing to proceeding through radical addition alkylation.

Language: Английский

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Regio- and Stereoselective Hexafluoroisopropoxylation and Trifluoroethoxylation of Allenamides

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(10), P. 7347 - 7351

Published: Jan. 2, 2024

Incorporating fluorinated moieties into organic molecules is an attractive strategy to enhance drug-like properties. Herein, we have developed a simple and self-promoted protocol for hexafluoroisopropoxylation trifluoroethoxylation of allenamides with alcohols such as HFIP TFE. The reaction provided the fluoroalkoxylated products in regio- stereoselective manner good moderate yields under mild conditions.

Language: Английский

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Modular Synthesis of α-Aryl Acrylamido Carboxylic Acids by Triple C–F Bond Cleavage of (Trifluoromethyl)alkenes with Unprotected Amino Acids

Organic Letters, Journal Year: 2024, Volume and Issue: 26(39), P. 8295 - 8300

Published: Sept. 23, 2024

A straightforward and efficient strategy for the construction of tertiary secondary α-aryl acrylamido carboxylic acids is reported. This N-acrylation protocol unprotected amino achieved by triple C-F bond cleavage (trifluoromethyl)alkenes. method features mild conditions, operationally simple, free transition metals racemization, can be used on a gram scale, compatible with various functional moieties. Mechanistic studies indicate that oxygen atom exchange happens among H

Language: Английский

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Mild defluorinative N-acrylation of amines with (trifluoromethyl)alkenes: synthesis of α-arylacrylamides

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 21, 2024

A practical and efficient method to access α-arylacrylamides via the N -acrylation of amines with (trifluoromethyl)alkenes cleavage three C(sp 3 )–F bonds is presented.

Language: Английский

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