Synthesis of S,S,O‑Orthoesters and 1,1-Difluoroalkyl Ethers via Reaction of Peroxides with Lithiated 1,3-Dithianes

Synthesis of S,S,O‑Orthoesters and 1,1-Difluoroalkyl Ethers via Reaction of Peroxides with Lithiated 1,3-Dithianes

Alkyl tetrahydropyranyl peroxides (ROOTHP) transfer alkoxide (OR) to lithiated 1,3-dithianes. The derived S,S,O-orthoesters undergo fluorodesulfurization with HF/pyridine and N-bromosuccinamide (NBS) to furnish difluoromethyl ethers. The overall protocol can be applied to synthesis of both terminal...

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Veröffentlicht in:Organic letters 2014-10, Vol.16 (20), p.5235-5237
Hauptverfasser: Kyasa, Shiva K., Dussault, Patrick H.
Format: Artikel
Sprache:eng
Schlagworte:
Ethers - chemical synthesis
Ethers - chemistry
Heterocyclic Compounds - chemistry
Molecular Structure
Peroxides - chemistry
Pyridines - chemistry
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Zusammenfassung:Alkyl tetrahydropyranyl peroxides (ROOTHP) transfer alkoxide (OR) to lithiated 1,3-dithianes. The derived S,S,O-orthoesters undergo fluorodesulfurization with HF/pyridine and N-bromosuccinamide (NBS) to furnish difluoromethyl ethers. The overall protocol can be applied to synthesis of both terminal (ROCF2H) and internal (ROCF2R′) ethers. Application of the same set of reactions to a lithiated tris(alkylthio)alkane is shown to generate a trifluoromethyl ether.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol502726p