Elsevier

Tetrahedron Letters

Volume 41, Issue 22, 8 June 2000, Pages 4463-4466
Tetrahedron Letters

Observations on the α-fluorination of α-phenylsulfanyl esters using difluoroiodotoluene

https://doi.org/10.1016/S0040-4039(00)00616-XGet rights and content

Abstract

α-Phenylsulfanyl esters are fluorinated in the α-position when treated with the hypervalent iodine reagent difluoroiodotoluene. Excess reagent can lead to α-fluoro sulfoxides, which can then undergo thermal syn elimination to produce vinyl fluorides.

Section snippets

Acknowledgements

We thank the EPSRC for the award of a studentship to M.F.G.

References (18)

  • McCarthey, J. R.; Peet, N. P.; LeTourneau, M. E.; Inbasekaran, M. J. Am. Chem. Soc. 1985, 107,...
  • (a) Wnuk, S. F.; Robins, M. J. J. Org. Chem. 1990, 55, 4757. (b) Robins, M. J.; Wnuk, S. F. J. Org. Chem. 1993, 58,...
  • (a) Zupan, M. J. Fluorine Chem. 1976, 8, 305. (b) Marat, R. K.; Janzen, A. F. Can. J. Chem. 1977, 55,...
  • Furuta, S.; Kuroboshi, M.; Hiyama, T. Bull. Chem. Soc. Jpn. 1998, 71,...
  • (a) Umemoto. T.; Tomizawa, G. Bull. Chem. Soc. Jpn. 1986, 59, 3625. (b) Sankar Lal, G. J. Org. Chem. 1993, 58,...
  • (a) Brigaud, T.; Laurent, E. Tetrahedron Lett. 1990, 31, 2287. (b) Fuchigami, T.; Higashiya, T.; Hou, Y.; Dawood, K. M....
  • (a) Sufrin, J. R.; Spiess, A. J.; Kramer, D. L.; Libby, P. R.; Porter, C. W. J. Med. Chem. 1989, 32, 997. (b) Lesuisse,...
  • Vaughn, M. D.; Cleve, P.; Robinson, V.; Duewel, H. S.; Honek, J. F. J. Am. Chem. Soc. 1999, 121,...
  • McCarthey, J. R.; Matthews, D. P.; Edwards, M. L.; Stemerick, D. M.; Jarvi, E. T. Tetrahedron Lett. 1990, 31, 5449 and...
There are more references available in the full text version of this article.

Cited by (33)

  • Organoiodine-induced hydroxylation as well as enantioselective alkoxylation/hydroxylation of allylic alcohols via 1,2- aryl migration

    2021, Tetrahedron
    Citation Excerpt :

    The chiral hypervalent iodine formed in situ from iodine benzene was applied to a series of enantioselective reactions [3]. Oxidative functionalization of allylic alcohols by oxidants DTBP(di-tert-butyl peroxide) [4], TBPB(tert-butylperoxybenzoate [5], TBHP(tert-Butyl hydroperoxide) [6] as well as hypervalent iodines like Togni's reagent [7] and iodobenzenediacetate [8] have also been reported. Most of these methods need high temperature to form the desired products with good yields, but high temperature is often unfavorable for the chiral synthesis [9].

  • Fluoro-Pummerer rearrangement and analogous reactions

    2012, Journal of Fluorine Chemistry
    Citation Excerpt :

    Among them the oxidative desulfurization–difluorination approach provides an efficient method for the synthesis of gem-difluorinated organic compounds [105,125]. Cyclic dithioacetals derived from aryl and alkyl aldehydes and ketones 156 were smoothly converted to gem-difluorides 157 using reagent combinations consisting of an oxidant such as DBH, NBS, NIS [126–128], SO2ClF [129] or NO+[BF4]− [111] and Py/HF, which are more easy to handle than the CF3OF/HF-combination constituted by Kollonitsch et al. [106] or a mixture of elemental iodine and fluorine [130] or BrF3 [131]. Recently, the combination of BrF3 and pyridine was shown to be a suitable reagent for this type of reactions, while BrF3 alone led to aromatic bromination or tarring [132].

  • Modern Pummerer-type reactions

    2006, Tetrahedron
    Citation Excerpt :

    The use of β-carbonyl-containing thionium ions in carbocyclization reactions directed toward natural product targets is illustrated in Scheme 17. Ikeda's concise synthesis of cephalotaxine (cf. 148) benefited enormously from the Pummerer reaction's ability to fashion seven-membered rings upon thionium ion initiated cyclization.60 The extension of this methodology beyond the common five- and six-membered ring domain (cf. 144 also) distinguishes Pummerer chemistry from many other acyclic closure strategies.

View all citing articles on Scopus
View full text