2,2‐Difluoroethylation of Heteroatom Nucleophiles via a Hypervalent Iodine Strategy

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Abstract: The 2,2‐difluoroethyl group is an important lipophilic hydrogen bond donor in medicinal chemistry, but its incorporation into small molecules is often challenging. Herein, we demonstrate electrophilic 2,2‐difluoroethylation of thiol, amine and alcohol nucleophiles with a hypervalent iodine reagent, (2,2‐difluoro‐ethyl)(aryl) iodonium triflate, via a proposed ligand coupling mechanism. This transformation offers a complementary strategy to existing 2,2‐difluoroethylation methods and allows access to a wide range of 2,2‐difluoroethylated nucleophiles, including the drugs Captopril, Normorphine and Mefloquine.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: 2,2‐Difluoroethylation of Heteroatom Nucleophiles via a Hypervalent Iodine Strategy ; day:08 ; month:08 ; year:2024 ; extent:7
Angewandte Chemie / International edition. International edition ; (08.08.2024) (gesamt 7)

Creator: Das, Suman
McIvor, Charlotte
Greener, Andrew
Suwita, Charlotte
Argent, Stephen P.
O'Duill, Miriam L.

DOI: 10.1002/anie.202410954

URN: urn:nbn:de:101:1-2408081430441.084242481631

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

Last update: 14.08.2025, 10:52 AM CEST

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Associated

Das, Suman
McIvor, Charlotte
Greener, Andrew
Suwita, Charlotte
Argent, Stephen P.
O'Duill, Miriam L.

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Hypervalent iodine-mediated intramolecular alkene halocyclisation

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Applications of hypervalent iodine(III) reagents in sulfoximidations

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Electrophilic Sulfoximidations of Thiols by Hypervalent Iodine Reagents

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Hypervalent iodine-mediated cyclization of bishomoallylamides to prolinols

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Enantioselective Oxidative Rearrangements with Chiral Hypervalent Iodine Reagents

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