Journal
ORGANIC LETTERS
Volume 16, Issue 20, Pages 5235-5237Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol502726p
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Funding
- NSF [CHE-1057982]
- NIH [RR016544]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1057982] Funding Source: National Science Foundation
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Alkyl tetrahydropyranyl peroxides (ROOTI-113) transfer alkoxide -THP(OR) to lithiated 1,3-dithianes. The derived S,S,O-orthoesters undergo 9-0 fluorodesulfurization with HF/pyridine and N-brornosuccinamide (NBS) to A2 furnish difluoromethyl ethers. The overall protocol can be applied to synthesis of both terminal (ROCF2H) and internal (ROCF2R1 ethers. Application of the same set of reactions to a fithiated tris(alkylthio)alkane is shown to generate a trifluoromethyl ether.
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