Abstract
Efficient and selective substitution of cyclic and acyclic vinyl ethers with photo-generated difluoromethyl radicals bearing ester and phosphonate groups, in the presence of 2,4,6-trimethylpyridine and diphenyl diselenide was successfully carried out to provide the corresponding regioselective unsaturated difluoromethylene adducts selectively. The reaction involves phenylselenyl transfer at an early stage followed by elimination of phenylselenol from the adducts once formed to provide the unsaturated difluoromethylene adducts selectively. This novel photochemical method was successfully extended to aromatic and heteroaromatic substitutions to provide the corresponding α-aryl-α,α-difluoroacetates and α-aryl-α,α- difluoromethylphosphonates in good to moderate yields.
Original language | English |
---|---|
Pages (from-to) | 3761-3769 |
Number of pages | 9 |
Journal | Tetrahedron |
Volume | 62 |
Issue number | 15 |
DOIs | |
Publication status | Published - 2006 Apr 10 |
Externally published | Yes |
Keywords
- C-CF bond formation
- Difluoromethyl radicals
- Group transfer
- Photoreaction
- Selenide
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry