Transition metal-catalyzed C(sp2/sp3)–H α-fluoroalkenylation from gem-(bromo/di)fluoroalkenes to monofluoroalkenes: scope, mechanisms, and synthetic applications

Eliwa, Essam M.; Bedair, Ahmed H.; Djukic, Jean-Pierre

doi:10.1039/d4ob01044b

Org. Biomol. Chem.

2024

DOI: 10.1039/d4ob01044b

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Transition metal-catalyzed C(sp²/sp³)–H α-fluoroalkenylation from gem-(bromo/di)fluoroalkenes to monofluoroalkenes: scope, mechanisms, and synthetic applications

Essam M. Eliwa,

Ahmed H. Bedair,

Jean-Pierre Djukic

Abstract: Organofluorines have a broad range of industrial applications, such as pharmaceutics, liquid crystal displays (LCD), solar cells, textiles, and construction coatings, and are used in peptidomimetics, surfactants, refrigerants, anesthetics, and...

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Chemo‐/Regioselective [5+1] Annulation with gem‐Difluoromethylene Allenes for the Assembly of Fluorinated 2H‐Chromenes and Dihydroquinolines

Lin,

Cai,

et al. 2024

Adv Synth Catal

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A variety of fluorinated 2H‐chromenes and dihydroquinolines was synthesized by virtue of gem‐difluoromethylene allenes as versatile coupling partners to participate in the transition metal‐catalysed cascade C‐H activation/[5+1] annulation of 2‐alkenylphenols/anilines. This protocol features specific chemo‐/regioselectivity, redox‐neutral manner and good compatibility, providing a straightforward synthetic route to intriguing motifs with the equipment of attractive fluoroalkenyl moiety. The distinctive gem‐difluorine effect induced an unexpected protonolysis of σ carbon‐metal bond, thus accounting for the observed selectivity via sequential C‐H activation/allene insertion/protonolysis/cyclization/β‐F elimination process.

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Chemo‐/Regioselective [5+1] Annulation with gem‐Difluoromethylene Allenes for the Assembly of Fluorinated 2H‐Chromenes and Dihydroquinolines

Lin,

Cai,

et al. 2024

Adv Synth Catal

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show abstract

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Transition metal-catalyzed C(sp²/sp³)–H α-fluoroalkenylation from gem-(bromo/di)fluoroalkenes to monofluoroalkenes: scope, mechanisms, and synthetic applications

Abstract: Organofluorines have a broad range of industrial applications, such as pharmaceutics, liquid crystal displays (LCD), solar cells, textiles, and construction coatings, and are used in peptidomimetics, surfactants, refrigerants, anesthetics, and...

Cited by 1 publication

References 74 publications

Chemo‐/Regioselective [5+1] Annulation with gem‐Difluoromethylene Allenes for the Assembly of Fluorinated 2H‐Chromenes and Dihydroquinolines

Chemo‐/Regioselective [5+1] Annulation with gem‐Difluoromethylene Allenes for the Assembly of Fluorinated 2H‐Chromenes and Dihydroquinolines

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