Photochemical substitution of olefins and aromatic compounds with difluoromethyl radicals bearing ester and phosphonate groups

Satoru Murakami, Hideki Ishii, Toshiki Tajima, Toshio Fuchigami

Research output: Contribution to journalArticle

67 Citations (Scopus)

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 languageEnglish
Pages (from-to)3761-3769
Number of pages9
JournalTetrahedron
Volume62
Issue number15
DOIs
Publication statusPublished - 2006 Apr 10
Externally publishedYes

Fingerprint

Bearings (structural)
Organophosphonates
Aromatic compounds
Alkenes
Esters
Substitution reactions

Keywords

  • C-CF bond formation
  • Difluoromethyl radicals
  • Group transfer
  • Photoreaction
  • Selenide

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Photochemical substitution of olefins and aromatic compounds with difluoromethyl radicals bearing ester and phosphonate groups. / Murakami, Satoru; Ishii, Hideki; Tajima, Toshiki; Fuchigami, Toshio.

In: Tetrahedron, Vol. 62, No. 15, 10.04.2006, p. 3761-3769.

Research output: Contribution to journalArticle

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