Electrochemical Vicinal Difluorination of Alkenes: Scalable and Amenable to Electron‐Rich Substrates †

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Abstract: Fluorinated alkyl groups are important motifs in bioactive compounds, positively influencing pharmacokinetics, potency and conformation. The oxidative difluorination of alkenes represents an important strategy for their preparation, yet current methods are limited in their alkene‐types and tolerance of electron‐rich, readily oxidized functionalities, as well as in their safety and scalability. Herein, we report a method for the difluorination of a number of unactivated alkene‐types that is tolerant of electron‐rich functionality, giving products that are otherwise unattainable. Key to success is the electrochemical generation of a hypervalent iodine mediator using an “ex‐cell” approach, which avoids oxidative substrate decomposition. The more sustainable conditions give good to excellent yields in up to decagram scales.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Electrochemical Vicinal Difluorination of Alkenes: Scalable and Amenable to Electron‐Rich Substrates † ; volume:132 ; number:3 ; year:2020 ; pages:1171-1176 ; extent:6
Angewandte Chemie ; 132, Heft 3 (2020), 1171-1176 (gesamt 6)

Creator: Doobary, Sayad
Sedikides, Alexi T.
Caldora, Henry P.
Poole, Darren L.
Lennox, Alastair

DOI: 10.1002/ange.201912119

URN: urn:nbn:de:101:1-2022053110002275155970

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:26 AM CEST

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Associated

Doobary, Sayad
Sedikides, Alexi T.
Caldora, Henry P.
Poole, Darren L.
Lennox, Alastair

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Three‐Component Radical Cross‐Coupling: Asymmetric Vicinal Sulfonyl‐Esterification of Alkenes Involving Sulfur Dioxide

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Electrochemical Vicinal Difluorination of Alkenes: Scalable and Amenable to Electron‐Rich Substrates †

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Hochschulschrift

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Enantioselective Vicinal Diacetoxylation of Alkenes under Chiral Iodine(III) Catalysis

Enantioselective Vicinal Diacetoxylation of Alkenes under Chiral Iodine(III) Catalysis

Electrochemical vicinal oxyazidation of α-arylvinyl acetates

Electrochemical vicinal oxyazidation of α-arylvinyl acetates

Metal-free visible-light-enabled vicinal trifluoromethyl dithiolation of unactivated alkenes

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Vicinal difunctionalization of alkenes by four-component radical cascade reaction of xanthogenates, alkenes, CO, and sulfonyl oxime ethers

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The Electrochemical cis ‐Chlorination of Alkenes

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Vicinal Difunctionalization of Unactivated Alkenes Through Radical Addition/Remote (Hetero) Aryl Migration Cascade

Vicinal Difunctionalization of Unactivated Alkenes Through Radical Addition/Remote (Hetero) Aryl Migration Cascade

Metal-free electrochemical dihydroxylation of unactivated alkenes

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Three‐Component Radical Cross‐Coupling: Asymmetric Vicinal Sulfonyl‐Esterification of Alkenes Involving Sulfur Dioxide

Three‐Component Radical Cross‐Coupling: Asymmetric Vicinal Sulfonyl‐Esterification of Alkenes Involving Sulfur Dioxide

Electrochemical Rearrangement for Remote Functionalizations of Unactivated Alkenes

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Electrochemical Borylation of Electron‐Deficient Alkenes and Allenoates

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Electrochemical Vicinal Difluorination of Alkenes: Scalable and Amenable to Electron‐Rich Substrates †

Electrochemical Vicinal Difluorination of Alkenes: Scalable and Amenable to Electron‐Rich Substrates †

Vicinal difunctionalisation of alkenes via I(I)/I(III) catalysis

Hochschulschrift

Vicinal difunctionalisation of alkenes via I(I)/I(III) catalysis

Enantioselective Vicinal Diacetoxylation of Alkenes under Chiral Iodine(III) Catalysis

Enantioselective Vicinal Diacetoxylation of Alkenes under Chiral Iodine(III) Catalysis

Electrochemical vicinal oxyazidation of α-arylvinyl acetates

Electrochemical vicinal oxyazidation of α-arylvinyl acetates

Metal-free visible-light-enabled vicinal trifluoromethyl dithiolation of unactivated alkenes

Metal-free visible-light-enabled vicinal trifluoromethyl dithiolation of unactivated alkenes

Vicinal difunctionalization of alkenes by four-component radical cascade reaction of xanthogenates, alkenes, CO, and sulfonyl oxime ethers

Vicinal difunctionalization of alkenes by four-component radical cascade reaction of xanthogenates, alkenes, CO, and sulfonyl oxime ethers

The Electrochemical cis ‐Chlorination of Alkenes

The Electrochemical cis ‐Chlorination of Alkenes

Vicinal Difunctionalization of Unactivated Alkenes Through Radical Addition/Remote (Hetero) Aryl Migration Cascade

Vicinal Difunctionalization of Unactivated Alkenes Through Radical Addition/Remote (Hetero) Aryl Migration Cascade

Metal-free electrochemical dihydroxylation of unactivated alkenes

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Three‐Component Radical Cross‐Coupling: Asymmetric Vicinal Sulfonyl‐Esterification of Alkenes Involving Sulfur Dioxide

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Electrochemical Rearrangement for Remote Functionalizations of Unactivated Alkenes

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Electrochemical Borylation of Electron‐Deficient Alkenes and Allenoates

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