Base-Mediated Regioselective [3 + 3] Annulation of Alkylidene Malononitriles with Trifluoromethyl Alkenes via Dual C–F Bond Cleavage DOI
Mingqiang Li, Weidi Zeng,

Ablimit Abdukader

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(35), P. 7452 - 7456

Published: Aug. 26, 2024

A base-mediated regioselective [3 + 3] annulation of alkylidene malononitriles with trifluoromethyl alkenes was described. The reaction proceeds through sequential intermolecular SN2′ and intramolecular SNV-type cyclization by cleaving dual C–F bonds in a group, which discriminate multiple carbon-nucleophilic sites using single base. Various bicycles bearing monofluorocyclohexene motif were assembled from readily available starting materials under mild conditions via one-pot cascade approach.

Language: Английский

Photoinduced Cobaloxime-Catalyzed Regio- and Diastereoselective Hydrogen-Evolution C(sp3)–H Phosphorylation of Bicyclo[1.1.0]butanes DOI
Pengfei Chen,

Meng-Yuan Dong,

Chun-Yu Han

et al.

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

Published: Jan. 15, 2025

Radical-initiated functionalization of bicyclo[1.1.0]butanes (BCBs) is a straightforward approach to accessing diverse cyclobutane derivatives. However, selective C(sp3)–H at the C2 position BCBs remains scarce. Herein, mild protocol for hydrogen-evolution phosphorylation with enabled by photoinduced cobaloxime catalysis was realized in regio- and diastereoselective manner. This oxidant- additional photocatalyst-free method wide range diarylphosphine oxides. The mechanism studied via control experiments DFT calculation. Moreover, efficiency this highlighted synthesis high-value, structurally complex molecules.

Language: Английский

Citations

0
Photocatalyzed/Base-Mediated Defluorinative Three-Component Cascade Cyclization: Access to Monofluorocyclohexenes and 6-Fluoro-1,2,3,4-tetrahydropyridines DOI

Shuyue Zhang,

Meixue Gan,

Fan Zhang

et al.

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

Published: March 19, 2025

A three-component cascade cyclization of α-CF3 alkenes, electron-rich and dimethyl esters or sulfonamides via a dual C–F bond cleavage process is described. This methodology provides general efficient strategy to access monofluorocyclohexenes 6-fluoro-1,2,3,4-tetrahydropyridines by switching the bifunctional reagents (dimethyl sulfonamides), which are valuable building blocks in synthetic chemistry pharmaceutical industries. The reaction mechanism applications products have been demonstrated.

Language: Английский

Citations

0
Base-Mediated Regioselective [3 + 3] Annulation of Alkylidene Malononitriles with Trifluoromethyl Alkenes via Dual C–F Bond Cleavage DOI
Mingqiang Li, Weidi Zeng,

Ablimit Abdukader

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(35), P. 7452 - 7456

Published: Aug. 26, 2024

A base-mediated regioselective [3 + 3] annulation of alkylidene malononitriles with trifluoromethyl alkenes was described. The reaction proceeds through sequential intermolecular SN2′ and intramolecular SNV-type cyclization by cleaving dual C–F bonds in a group, which discriminate multiple carbon-nucleophilic sites using single base. Various bicycles bearing monofluorocyclohexene motif were assembled from readily available starting materials under mild conditions via one-pot cascade approach.

Language: Английский

Citations

2