Synthesis of Selectively gem-Difluorinated Molecules; Chiral gem-Difluorocyclopropanes via Chemo-Enzymatic Reaction and gem-Difluorinated Compounds via Radical Reaction.
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DOI: 10.1002/tcr.202300028
Abstract: The incorporation of fluorine atoms into an organic compound can alter the chemical reactivity or biological activity of the resulting compound due to the strong electron withdrawing nature of the fluorine atom. We have synthesized… read more here.
Keywords: gem difluorocyclopropanes; gem difluorinated; gem; reaction ... See more keywords
Divergent Synthesis of gem-Difluorinated Oxa-Spirocyclohexadienones by One-Pot Sequential Reactions of p-Hydroxybenzyl Alcohols with Difluoroenoxysilanes.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c00550
Abstract: A new efficient formal [2 + 3] cyclization of p-hydroxybenzyl alcohols with difluoroenoxysilanes has been established. This convenient one-pot sequential procedure enables the divergent construction of highly functionalized gem-difluorinated oxa-spirocyclohexadienones under mild conditions. As opposed… read more here.
Keywords: difluorinated oxa; alcohols difluoroenoxysilanes; gem difluorinated; one pot ... See more keywords
Regio- and Stereoselective Addition to gem-Difluorinated Ene-Ynamides: Access to Stereodefined Fluorinated Dienes.
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DOI: 10.1021/acs.orglett.2c01593
Abstract: The first synthesis of gem-difluorinated ene-ynamides is presented via deprotonation of trifluoromethylated N-allenamides and δ extrusion of fluorine. These highly reactive building blocks, owing to their dual functional groups, offer a unique entry to difluorinated… read more here.
Keywords: addition; gem difluorinated; ene ynamides; difluorinated ene ... See more keywords
Synthesis of gem-Difluorinated 1,3-Dienes via Synergistic Cu/Pd-Catalyzed Borodifluorovinylation of Alkynes.
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DOI: 10.1021/acs.orglett.2c01875
Abstract: gem-Difluoroalkenes (=CF2), which normally act as metabolically stable bioisosteres for carbonyl groups (C═O), are widely applied in agrochemicals and pharmaceuticals and are also used as building blocks in organic synthesis. Herein, an example of Cu/Pd-catalyzed… read more here.
Keywords: gem difluorinated; gem; catalyzed borodifluorovinylation; difluorinated dienes ... See more keywords
Enantioselective Formation of All-Carbon Quaternary Stereocenters in gem-Difluorinated Cyclopropanes via Rhodium-Catalyzed Stereoablative Kinetic Resolution.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c02410
Abstract: Herein, we report an effective method to offer chiral gem-difluorinated cyclopropanes containing an all-carbon quaternary stereocenter by rhodium-catalyzed stereoablative kinetic resolution. The activation of a sterically hindered all-carbon quaternary C-C bond through oxidative addition with… read more here.
Keywords: rhodium catalyzed; gem difluorinated; difluorinated cyclopropanes; carbon quaternary ... See more keywords
Fluoro-Promoted Thermal Ring Expansion of Cyclopropyl Carbenes to gem-Difluorinated Cyclobutenes.
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DOI: 10.1021/acs.orglett.4c03920
Abstract: Synthesis of gem-difluorinated cyclobutenes presents certain challenges for considering the compatibility of the fluorine atom introduction with four-membered ring retention. Herein, we develop a transition-metal-free synthetic strategy toward gem-difluorinated cyclobutenes from gem-difluorinated cyclopropyl N-tosylhydrazons via… read more here.
Keywords: difluorinated cyclobutenes; gem; gem difluorinated; cyclopropyl carbenes ... See more keywords
Palladium-Catalyzed Dearomative Fluoroallylation of Pyrroles with gem-Difluorinated Cyclopropanes.
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DOI: 10.1021/acs.orglett.5c00817
Abstract: We herein report the development of a novel Pd-catalyzed dearomative functionalization of pyrroles with gem-difluorinated cyclopropanes (gem-F2CPs). This dearomative/ring-opening strategy streamlines the diversity-oriented synthesis (DOS) of α-quaternary 2-fluoroallylic 2H-pyrroles with a broad scope and excellent… read more here.
Keywords: palladium catalyzed; difluorinated cyclopropanes; dearomative fluoroallylation; gem difluorinated ... See more keywords
Metal-free synthesis of gem-difluorinated heterocycles from enaminones and difluorocarbene precursors.
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DOI: 10.1039/d2cc00383j
Abstract: A cascade strategy to synthesise gem-difluorinated 2H-furans from reactions of BrCF2CO2Et with enaminones has been described. The reactions tolerate a wide variety of functional groups under metal-free conditions. An active aminocyclopropane is proposed to be… read more here.
Keywords: gem difluorinated; gem; metal free; free synthesis ... See more keywords