Regioselective polyfluoroarylation of alkenyl C–H bonds via aryl to vinyl 1,4-palladium migration

Lin, Jie; Ma, Juan; Wang, Liandi; Wu, Kaikai; Zhou, Yong-Gui; Yu, Zhengkun

doi:10.1039/d3qo01099f

Org. Chem. Front.

2023

DOI: 10.1039/d3qo01099f

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Regioselective polyfluoroarylation of alkenyl C–H bonds via aryl to vinyl 1,4-palladium migration

Jie Lin,

Juan Ma,

Liandi Wang

et al.

Abstract: Efficient palladium-catalyzed regioselective vinylic C–H polyfluoroarylation of gem-disubstituted ethylenes with polyfluoroarenes was realized via an aryl to vinyl 1,4-palladium migration process to access various polyfluorinated triarylethenes.

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2024

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Cited by 3 publications

References 42 publications

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Stereoselective Construction of Trisubstituted 1,3‐Enynes via Aryl to Vinyl 1,4‐Palladium Migration

Lin,

Ma,

Wang

et al. 2024

Adv Synth Catal

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Palladium‐catalyzed stereoselective olefinic C–H alkynylation of gem‐diarylsubstituted ethylenes with propargylic alcohols was achieved to access diverse unsymmetrical 1,3‐enynes. The regio‐ and stereoselectivities were established through a 1,4‐palladium migration from aryl to vinyl in the presence of 2‐FC6H4OH additive. Mechanistic investigations have suggested that cleavage of the olefinic C–H bond might not be involved in the rate‐determining step throughout the catalytic process.

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Stereoselective Construction of Trisubstituted 1,3‐Enynes via Aryl to Vinyl 1,4‐Palladium Migration

Lin,

Ma,

Wang

et al. 2024

Adv Synth Catal

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show abstract

Highly Stereoselective Synthesis of 1,3‐Enynes via Aryl to Vinyl 1,4‐Palladium Migration/Sonogashira Coupling Sequence

Chen,

Ji,

Wang

et al. 2024

ChemCatChem

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Recent progress in metal-catalyzed C(sp³)-P bond formation

Tu,

Shen,

Huang

2024

Tetrahedron

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Regioselective polyfluoroarylation of alkenyl C–H bonds via aryl to vinyl 1,4-palladium migration

Abstract: Efficient palladium-catalyzed regioselective vinylic C–H polyfluoroarylation of gem-disubstituted ethylenes with polyfluoroarenes was realized via an aryl to vinyl 1,4-palladium migration process to access various polyfluorinated triarylethenes.

Cited by 3 publications

References 42 publications

Stereoselective Construction of Trisubstituted 1,3‐Enynes via Aryl to Vinyl 1,4‐Palladium Migration

Stereoselective Construction of Trisubstituted 1,3‐Enynes via Aryl to Vinyl 1,4‐Palladium Migration

Highly Stereoselective Synthesis of 1,3‐Enynes via Aryl to Vinyl 1,4‐Palladium Migration/Sonogashira Coupling Sequence

Recent progress in metal-catalyzed C(sp³)-P bond formation

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