Facile Conversion of Alcohols to the Corresponding 2,2,2-Trifluoroethyl Esters with Molecular Iodine and Potassium Carbonate in 2,2,2-Trifluoro­ethanol

Naoshi Mori; Hideo Togo

doi:10.1055/s-2004-817789

LETTER

Facile Conversion of Alcohols to the Corresponding 2,2,2-Trifluoroethyl Esters with Molecular Iodine and Potassium Carbonate in 2,2,2-Trifluoroethanol

Naoshi Mori^a, Hideo Togo*^a,b
^a Graduate School of Science and Technology, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan
^b Department of Chemistry, Faculty of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan
e-Mail: togo@faculty.chiba-u.jp;

Abstract

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Abstract

A simple, effective, and high-yield procedure for the oxidative conversion of primary alcohols to the corresponding 2,2,2-trifluoroethyl esters, with molecular iodine and potassium carbonate in 2,2,2-trifluoroethanol, was studied.

Key words

molecular iodine - oxidation - alcohol - aldehyde - 2,2,2-trifluoroethyl ester

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Referenzen

References

<A NAME="RU01404ST-1A">1a</A> Larock RC. Comprehensive Organic Transformation VCH; New York: 1989.

<A NAME="RU01404ST-1B">1b</A> Hudlicky M. Oxidations in Organic Chemistry American Chemical Society; Washington / D. C.: 1990.

<A NAME="RU01404ST-2A">2a</A> Meyers CY. J. Org. Chem. 1961, 26: 1046

<A NAME="RU01404ST-2B">2b</A> Lee GA. Freedman HH. Tetrahedron Lett. 1976, 1641

<A NAME="RU01404ST-2C">2c</A> Regan SL. J. Org. Chem. 1977, 42: 875

<A NAME="RU01404ST-2D">2d</A> Stevens RV. Chapman KT. Weller HN. J. Org. Chem. 1980, 45: 2030

<A NAME="RU01404ST-2E">2e</A> Nwaukwa SO. Keehn PM. Tetrahedron Lett. 1982, 23: 3131

<A NAME="RU01404ST-2F">2f</A> Wilson SR. Tofigh S. Misra RN. J. Org. Chem. 1982, 47: 1360

<A NAME="RU01404ST-3">3</A> Stevens RV. Chapman KT. Stubbs CA. Tam WW. Albizati KF. Tetrahedron Lett. 1982, 23: 4647

<A NAME="RU01404ST-4A">4a</A> Corey EJ. Kim CU. J. Am. Chem. Soc. 1972, 94: 7586

<A NAME="RU01404ST-4B">4b</A> Corey EJ. Kim CU. J. Org. Chem. 1973, 38: 1233

<A NAME="RU01404ST-4C">4c</A> Corey EJ. Kim CU. Tetrahedron Lett. 1973, 919

<A NAME="RU01404ST-4D">4d</A> Wicha J. Zarecki A. Tetrahedron Lett. 1974, 3059

<A NAME="RU01404ST-4E">4e</A> Grosby GA. Weinshenker NM. Uh H.-S.
J. Am. Chem. Soc. 1975, 97: 2232

<A NAME="RU01404ST-5A">5a</A> Perlmutter-Hayman B. Weissmann Y. J. Am. Chem. Soc. 1969, 91: 668

<A NAME="RU01404ST-5B">5b</A> Neirabeyeh MA. Ziegler J.-C. Gross B. Synthesis 1976, 811

<A NAME="RU01404ST-6A">6a</A> Inch TD. Ley RV. Rich P. J. Chem. Soc. C 1968, 1693

<A NAME="RU01404ST-6B">6b</A> Eliel EL. Clawson L. Knox DE. J. Org. Chem. 1985, 50: 2707

<A NAME="RU01404ST-6C">6c</A> Yamada S. Morizono D. Yamamoto K. Tetrahedron Lett. 1992, 33: 4329

<A NAME="RU01404ST-6D">6d</A> Talukdar S. Hsu J.-L. Chou T.-C. Fang J.-M. Tetrahedron Lett. 2001, 42: 1103

<A NAME="RU01404ST-7">7</A> Lieben A. Annals 1870, 7: 218

<A NAME="RU01404ST-8A">8a</A> Togo H. Katohgi M. Synlett 2000, 565

<A NAME="RU01404ST-8B">8b</A> Togo H. Harada Y. Yokoyama M. J. Org. Chem. 2000, 65: 926

<A NAME="RU01404ST-8C">8c</A> Katohgi M. Togo H. Tetrahedron 2001, 57: 7481

<A NAME="RU01404ST-9">9</A> Shono T. Matsumura Y. Hayashi J. Mizoguchi M. Tetrahedron Lett. 1979, 165

<A NAME="RU01404ST-10">10</A> DeTar DF. J. Am. Chem. Soc. 1982, 104: 7205

<A NAME="RU01404ST-11A">11a</A> Kesavan V. Bonnet-Delpon D. Bégué J.-P. Synthesis 2000, 223

<A NAME="RU01404ST-11B">11b</A> Neimann K. Neumann R. Org. Lett. 2000, 2: 2861

<A NAME="RU01404ST-11C">11c</A> van Vliet MCA. Arends IWC. Sheldon RA. Synlett 2001, 248

<A NAME="RU01404ST-11D">11d</A> de Visser SP. Kaneti J. Neumann R. Shaik S. J. Org. Chem. 2003, 68: 2903

<A NAME="RU01404ST-11E">11e</A> Chikaoka S. Toyao A. Ogasawara M. Tamura O. Ishibashi H. J. Org. Chem. 2003, 68: 312

<A NAME="RU01404ST-11F">11f</A> Harmata M. Lee DR. J. Am. Chem. Soc. 2002, 124: 14328

<A NAME="RU01404ST-11G">11g</A> Abe M. Adam W. Minamoto T. Ino Y. Nojima M. J. Org. Chem. 2003, 68: 1796

<A NAME="RU01404ST-11H">11h</A> Grainger RS. Owoare RB. Tisselli P. Steed JW. J. Org. Chem. 2003, 48: 7899

<A NAME="RU01404ST-11I">11i</A> Ben-Daniel R. de Visser SP. Shaik S. Neumann R. J. Am. Chem. Soc. 2003, 125: 12116

<A NAME="RU01404ST-11J">11j</A> Iskra J. Bonnet-Delpon D. Bégué J.-P. Tetrahedron Lett. 2003, 44: 6309

<A NAME="RU01404ST-12">12</A> Miller RA. Hoerrner RS. Org. Lett. 2003, 5: 285

All the compounds gave satisfactory spectroscopic and microanalytical data.

<A NAME="RU01404ST-14">14</A> Kubota T. Miyashita S. Kitazume T. Ishikawa N.
J. Org. Chem. 1980, 45: 5052

Facile Conversion of Alcohols to the Corresponding 2,2,2-Trifluoroethyl Esters with Molecular Iodine and Potassium Carbonate in 2,2,2-Trifluoro­ethanol

Facile Conversion of Alcohols to the Corresponding 2,2,2-Trifluoroethyl Esters with Molecular Iodine and Potassium Carbonate in 2,2,2-Trifluoroethanol