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Synlett 2018; 29(04): 415-418
DOI: 10.1055/s-0036-1589119
DOI: 10.1055/s-0036-1589119
cluster
Iodine Monoacetate for Efficient Oxyiodinations of Alkenes and Alkynes
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).Weitere Informationen
Publikationsverlauf
Received: 06. September 2017
Accepted after revision: 27. September 2017
Publikationsdatum:
20. Oktober 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
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1589119.
- Supporting Information
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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
- 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