Transition-Metal-Free Hydrodefluoroamination of Trifluoromethyl Enones for the Synthesis of α-Fluoroenamides DOI

Ya‐Fei Hu,

M Kellis,

Ming-Yao Tang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 10299 - 10310

Published: July 2, 2024

A three-component strategy was developed to enable hydrodefluoroamination of β-trifluoromethyl enones by selectively activating two C(sp3)-F bonds in the trifluoromethyl group. The method involved a sequence carbonyl reduction, hydrodefluorination, and defluoroamination under transition-metal-free conditions. Synthetically useful (E)-stereospecific α-fluoroenamides were obtained good yields with diverse functional group tolerance, which could be easily transformed into valuable organofluorides heterocycles. auxiliary exerts both electronic steric impacts on CF3-alkenes, allowing for controllable selective defluorination.

Language: Английский

Multi-functionalization of β-trifluoromethyl enones enabled 2,3-dihydrofuran synthesis DOI

Ya-Fei Hu,

Wei Han,

Ye-Kun Chen

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(18), P. 5144 - 5150

Published: Jan. 1, 2024

A transition-metal-free multi-functionalization reaction of β-trifluoromethyl enones and azacycles is first developed for the synthesis valuable amino-2,3-dihydrofuran derivatives.

Language: Английский

Citations

4
Three-Component Sulfonylation and Heteroannulation Enabled by 3-Fold Defluorofunctionalization of Trifluoromethyl Enones DOI

Shu-Ji Gao,

Xueying Huang, M Kellis

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 23, 2025

Trifluoromethyl enone emerges as a versatile and multifaceted building block in organic synthesis. A defluorinative heterocyclization reaction of readily available β,β-ditrifluoromethylated enones biocompatible sodium sulfinates has been developed for the modular synthesis densely functionalized furans with regio-defined C2,4-bissulfonyl C3-trifluoromethyl substitutions. This three-component method proceeds through sequential sulfonylation intramolecular O-cyclization, enabling assembly one furan ring, formation C-SO2/C–O bonds, cleavage three C(sp3)-F bonds one-pot manner under transition metal-free conditions. Moreover, obtained product can further react benzyne precursor to generate 1,4-epoxynaphthalene Diels–Alder cycloaddition. The is also distinguished by its broad substrate scope, excellent functional group tolerance, scalability.

Language: Английский

Citations

0
Direct Access to CF3-Containing 4H-1,3-Oxazines and 2-Aminopyrimidines Via a [4 + 2] Annulation Using In Situ Generated Carbodiimide Anions DOI
Huamin Wang,

Wenjing Niu,

Wei Min

et al.

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

Published: March 11, 2025

The carbodiimide anions which were generated in situ from N-cyano-N-aryl-p-toluenesulfonamides (NCTS) the presence of base participated annulations that remain less reported to date. Herein, we have developed for first time an efficient and environmentally friendly [4 + 2] annulation reaction CF3-substituted hetero-1,3-dienes with NCTS synthesis 4H-1,3-oxazines 2-aminopyrimidines under transition-metal-free conditions. methodology demonstrates advantages readily available substrates, simple operation, good functional group tolerance, broad substrate scope, providing a promising route structurally diverse scaffolds. products followed by transformations provide facile TAS2R14 agonist analogues.

Language: Английский

Citations

0
Transition-Metal-Free Hydrodefluoroamination of Trifluoromethyl Enones for the Synthesis of α-Fluoroenamides DOI

Ya‐Fei Hu,

M Kellis,

Ming-Yao Tang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 10299 - 10310

Published: July 2, 2024

A three-component strategy was developed to enable hydrodefluoroamination of β-trifluoromethyl enones by selectively activating two C(sp3)-F bonds in the trifluoromethyl group. The method involved a sequence carbonyl reduction, hydrodefluorination, and defluoroamination under transition-metal-free conditions. Synthetically useful (E)-stereospecific α-fluoroenamides were obtained good yields with diverse functional group tolerance, which could be easily transformed into valuable organofluorides heterocycles. auxiliary exerts both electronic steric impacts on CF3-alkenes, allowing for controllable selective defluorination.

Language: Английский

Citations

0