Synlett 2018; 29(04): 415-418
DOI: 10.1055/s-0036-1589119
cluster
© Georg Thieme Verlag Stuttgart · New York

Iodine Monoacetate for Efficient Oxyiodinations of Alkenes and Alkynes

Tobias Hokamp
a   School of Chemistry, Cardiff University, Park Place, Cardiff, CF10 3AT, UK   Email: wirth@cf.ac.uk
,
Alena Therese Storm
a   School of Chemistry, Cardiff University, Park Place, Cardiff, CF10 3AT, UK   Email: wirth@cf.ac.uk
,
Mekhman Yusubov
b   Tomsk Polytechnic University and Siberian State Medical University, 634050 Tomsk, Russia
,
Thomas Wirth*
a   School of Chemistry, Cardiff University, Park Place, Cardiff, CF10 3AT, UK   Email: wirth@cf.ac.uk
› Author Affiliations
Support from the Fonds der Chemischen Industrie (TH), the Erasmus program (ATS), and the School of Chemistry, Cardiff University, is gratefully acknowledged. We thank the Russian Foundation for Basic Research (RFBR-KO_a 16-53-10046) and the Royal Society (IE160304) for support. Financial support from Tomsk Polytechnic University (VIU-316/2017) is also gratefully acknowledged (MY).
Further Information

Publication History

Received: 06 September 2017

Accepted after revision: 27 September 2017

Publication Date:
20 October 2017 (online)


Published as part of the Cluster Alkene Halofunctionalization

Abstract

A novel and inexpensive, environmentally friendly method for the preparation of iodine monoacetate is presented using iodine and Oxone in acetic acid/acetic anhydride. The reagent is used in a highly efficient approach for the regio- and diastereoselective iodo­acetoxylation of alkenes and alkynes in a simple one-pot process.

Supporting Information

 
  • References and Notes

    • 1a Ginsburg D. J. Am. Chem. Soc. 1953; 75: 5746
    • 1b Heasley VL. Holstein III LS. Moreland RJ. Rosbrugh JW. Jr. Shellhamer DF. J. Chem. Soc., Perkin Trans. 2 1991; 1271
    • 1c Dhaliwal GK. Wilson GJ. Rubber Chem. Technol. 1994; 67: 567
    • 1d Ogata Y. Aoki K. J. Org. Chem. 1966; 31: 1625
    • 1e Giri R. Yu J.-Q. Iodine Monoacetate, e-EROS Encyclopedia of Reagents for Organic Synthesis . John Wiley and Sons; Hoboken, NJ: 2008
    • 2a Kleinberg J. Chem. Rev. 1947; 40: 381
    • 2b Wilson CV. Org. React. 1957; 9: 332
    • 3a Simonini A. Monatsh. Chem. 1893; 14: 81
    • 3b Bunce NJ. Murray NG. Tetrahedron 1971; 27: 5323
  • 4 Courtneidge JL. Lusztyk J. Pagé D. Tetrahedron Lett. 1994; 35: 1003
  • 5 Barnett JR. Andrews LJ. Keefer RM. J. Am. Chem. Soc. 1972; 94: 6129
  • 6 Chen EM. Keefer RM. Andrews LJ. J. Am. Chem. Soc. 1967; 89: 428
  • 7 Heusler K. Kalvoda J. Angew. Chem., Int. Ed. Engl. 1964; 3: 525
  • 8 Ogata Y. Aoki K. J. Am. Chem. Soc. 1968; 90: 6187
  • 9 Reddy MM. Kumar MA. Swamy P. Narender N. Tetrahedron Lett. 2011; 52: 6554
  • 10 Durgaiah C. Naresh M. Kumar MA. Swamy P. Reddy MM. Srujana K. Narender N. Synth. Commun. 2016; 46: 1133
  • 11 Zhu M. Zhao Y. Chin. Chem. Lett. 2015; 26: 248
  • 12 Monenschein H. Sourkouni-Argirusi G. Schubothe KM. O’Hare T. Kirschning A. Org. Lett. 1999; 1: 2101
  • 13 Terent’ev AO. Borisov DA. Krylov IB. Kikishin GI. Synth. Commun. 2007; 37: 3151