2,2‐Difluoroethylation of Heteroatom Nucleophiles via a Hypervalent Iodine Strategy
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.
- Standort
-
Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
-
Online-Ressource
- Sprache
-
Englisch
- Erschienen in
-
2,2‐Difluoroethylation of Heteroatom Nucleophiles via a Hypervalent Iodine Strategy ; day:08 ; month:08 ; year:2024 ; extent:7
Angewandte Chemie ; (08.08.2024) (gesamt 7)
- Urheber
-
Das, Suman
McIvor, Charlotte
Greener, Andrew
Suwita, Charlotte
Argent, Stephen P.
O'Duill, Miriam L.
- DOI
-
10.1002/ange.202410954
- URN
-
urn:nbn:de:101:1-2408081432103.126141089739
- Rechteinformation
-
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
-
14.08.2025, 11:02 MESZ
Datenpartner
Dieses Objekt wird bereitgestellt von:
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Beteiligte
- Das, Suman
- McIvor, Charlotte
- Greener, Andrew
- Suwita, Charlotte
- Argent, Stephen P.
- O'Duill, Miriam L.
Ähnliche Objekte (12)
2,2‐Difluoroethylation of Heteroatom Nucleophiles via a Hypervalent Iodine Strategy
Hypervalent Iodine for α,α-Dihalogenation
Hypervalent iodine-mediated intramolecular alkene halocyclisation
Thioamination of Alkenes with Hypervalent Iodine Reagents
Hypervalent iodine chemistry : modern developments in organic synthesis
Applications of hypervalent iodine(III) reagents in sulfoximidations
Electrophilic Sulfoximidations of Thiols by Hypervalent Iodine Reagents
Electrophilic Sulfoximidations of Thiols by Hypervalent Iodine Reagents
Synthesis of spirocyclic scaffolds using hypervalent iodine reagents
Enantioselective Oxidative Rearrangements with Chiral Hypervalent Iodine Reagents
Hypervalent iodine-mediated cyclization of bishomoallylamides to prolinols
Hypervalent Iodine‐Mediated Late‐Stage Peptide and Protein Functionalization
2,2‐Difluoroethylation of Heteroatom Nucleophiles via a Hypervalent Iodine Strategy
Hypervalent Iodine for α,α-Dihalogenation
Hypervalent iodine-mediated intramolecular alkene halocyclisation
Thioamination of Alkenes with Hypervalent Iodine Reagents
Hypervalent iodine chemistry : modern developments in organic synthesis
Applications of hypervalent iodine(III) reagents in sulfoximidations
Electrophilic Sulfoximidations of Thiols by Hypervalent Iodine Reagents
Electrophilic Sulfoximidations of Thiols by Hypervalent Iodine Reagents
Synthesis of spirocyclic scaffolds using hypervalent iodine reagents
Enantioselective Oxidative Rearrangements with Chiral Hypervalent Iodine Reagents
Hypervalent iodine-mediated cyclization of bishomoallylamides to prolinols
Hypervalent Iodine‐Mediated Late‐Stage Peptide and Protein Functionalization
2,2‐Difluoroethylation of Heteroatom Nucleophiles via a Hypervalent Iodine Strategy
Hypervalent Iodine for α,α-Dihalogenation
Hypervalent iodine-mediated intramolecular alkene halocyclisation
Thioamination of Alkenes with Hypervalent Iodine Reagents
Hypervalent iodine chemistry : modern developments in organic synthesis
Applications of hypervalent iodine(III) reagents in sulfoximidations
Electrophilic Sulfoximidations of Thiols by Hypervalent Iodine Reagents
Electrophilic Sulfoximidations of Thiols by Hypervalent Iodine Reagents
Synthesis of spirocyclic scaffolds using hypervalent iodine reagents
Enantioselective Oxidative Rearrangements with Chiral Hypervalent Iodine Reagents
Hypervalent iodine-mediated cyclization of bishomoallylamides to prolinols