Alkene Vicinal Difluorination: From Fluorine Gas to More Favoured Conditions

Doobary, Sayad; Lennox, Alastair J. J.

doi:10.1055/s-0040-1707143

Cited by 11 publications

(2 citation statements)

References 62 publications

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“…with moderate yields. Notably, a wide range of functional groups (FGs), including bromo (26,30), phthalimide (27,28), sulfonate ester (31,32), benzoate (33), sulfonic ester (34), phenyl ether (35), methyl ester (36), and chloro (38) on the alkyl chain, remained unreacted, indicating the high chemoselectivity and mild reaction conditions of the protocol. To further assess the compatibility of this method in more structurally complex contexts, several natural products and biologically active compounds containing indoles were subjected to the reaction.…”

Section: Resultsmentioning

confidence: 99%

“…29 Consequently, there has been significant research focus on the synthesis of vicinal difluoroalkanes in recent years. 30 Among the various synthetic methodologies, the direct difluorination of olefins using iodine(I)/(III) catalysis stands out as a particularly appealing approach. [31][32][33][34][35][36][37] https://doi.org/10.26434/chemrxiv-2023-kd4f3 ORCID: https://orcid.org/0000-0002-9648-6759 Content not peer-reviewed by ChemRxiv.…”

Section: Introductionmentioning

confidence: 99%

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Catalytic, Dearomative 2,3-Difluorination of Indoles

Tu,

Lin,

Tang

et al. 2023

Preprint

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Indolines, characterized by their diverse biological activities and structural significance, have garnered considerable attention in the realms of natural product synthesis and drug discovery. Concurrently, the incorporation of fluorine atoms into organic molecules has emerged as a powerful strategy to enhance their pharmacological properties. Herein, we report a robust and diastereoselective approach for the synthesis of 2,3-difluorinated indolines through the iodine(I/III)-catalyzed dearomatization of readily available indoles. The protocol operates under mild conditions, displaying excellent functional group tolerance and remarkable diastereoselectivity. By employing this developed protocol, vicinal-difluorinated analogues of indole-containing drugs can be efficiently accessed. Theoretical calculations have shed light on the underlying reaction mechanism, proposing the formation of a β-fluorine-substituted carbocation intermediate. It is postulated that the observed high diastereoselectivity can be attributed to the dipole-dipole interactions facilitated by the C-F bond. Crystallographic analysis has revealed the profound impact of fluorine atom introduction on the conformational preferences of the indoline core. Given the unique structural characteristics and pharmacological significance of 2,3-difluorinated indolines, we anticipate their widespread application in medicinal chemistry and drug discovery endeavors.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Catalytic, Dearomative 2,3-Difluorination of Indoles

Tu,

Lin,

Tang

et al. 2023

Preprint

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3D Printed Reactionware for Synthetic Electrochemistry with Hydrogen Fluoride Reagents

2021

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Electrochemical fluorination reactions of organic compounds frequently employ hydrogen fluoride reagents that are corrosive. The corrosive nature of these reagents necessitates either the construction or purchase of cells that are stable to hydrogen fluoride, which require high-cost materials, machining time and expertise. Herein, we offer an alternative solution using 3D printing, which is an inexpensive and rapid manufacturing technique. We have designed, printed and shared four different cell types in polypropylene and tested them in an electrochemical alkene difluorination reaction in the presence of triethylamine • 3HF and pyridinium poly • (HF).

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Enantioselective Dihalogenation of Alkenes

Bock

Guria

Wedek

et al. 2021

Chemistry A European J

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The dihalogenation of alkenes is one of the classic reactions in organic chemistry and a prime example of an electrophilic addition reaction. The often observed anti‐selectivity in this addition reaction can be explained by the formation of a haliranium‐ion intermediate. Although dihalogenations have been studied for more than a century, the development of reagent‐controlled, enantioselective dihalogenation has proved to be very difficult. Only recently, significant progress has been achieved. In this review, an overview on current method development in enantioselective dihalogenation is provided and mechanistic aspects that render this transformation challenging are discussed.

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Alkene Vicinal Difluorination: From Fluorine Gas to More Favoured Conditions

Cited by 11 publications

References 62 publications

Catalytic, Dearomative 2,3-Difluorination of Indoles

Catalytic, Dearomative 2,3-Difluorination of Indoles

3D Printed Reactionware for Synthetic Electrochemistry with Hydrogen Fluoride Reagents

Enantioselective Dihalogenation of Alkenes

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