Abstract
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. (Chemical Equation Presented).
Original language | English (US) |
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Pages (from-to) | 5235-5237 |
Number of pages | 3 |
Journal | Organic Letters |
Volume | 16 |
Issue number | 20 |
DOIs | |
State | Published - Oct 17 2014 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry