PDF icon PDF herunterladen
Synthesis 2012(8): 1226-1232  
DOI: 10.1055/s-0031-1289750
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Novel One-Pot Method for α-Tosyloxylation of Ketones Using a Catalytic Amount of Ammonium Iodide

Jiantao Hua, Min Zhub, Yuan Xua, Jie Yan*a
a College of Chemical Engineering and Materials Sciences, Zhejiang University of Technology, Hangzhou 310032, P. R. of China
Fax: +86(571)88320238; e-Mail: jieyan87@zjut.edu.cn;
b College of Biological and Environmental Sciences, Zhejiang Shuren University, Hangzhou 310015, P. R. of China
Weitere Informationen

Publikationsverlauf

Received 14 January 2012
Publikationsdatum:
15. März 2012 (online)

   Lizenzen und Reprints Alle Artikel dieser Rubrik
Preview

Abstract

A novel one-pot procedure was designed for the preparation of various α-tosyloxy ketones in good yields by the reaction of ketones with m-chloroperoxybenzoic acid and p-toluenesulfonic acid monohydrate in the presence of catalytic amounts of ammonium iodide and benzene in a mixture of acetonitrile and 2,2,2-trifluo­roethanol (8:2) at room temperature for 24 hours.

Key words

α-tosyloxylation - α-tosyloxy ketones - hypervalent iodine intermediate - ammonium iodide

    References

  • 1a Varvoglis A. Tetrahedron  1997,  53:  1179 
    Suche in Google Scholar
  • 1b Stang PJ. Zhdankin VV. Chem. Rev.  1996,  96:  1123 
    Suche in Google Scholar
  • 1c Zhdankin VV. Stang PJ. Chem. Rev.  2002,  102:  2523 
    Suche in Google Scholar
  • 1d Kirschning A. Eur. J. Org. Chem.  1998,  2267 
  • 1e Ochiai M. J. Organomet. Chem.  2000,  611:  494 
    Suche in Google Scholar
  • 1f Okuyama T. Acc. Chem. Res.  2002,  35:  12 
    Suche in Google Scholar
  • 1g Zhdankin VV. Stang PJ. Tetrahedron  1998,  54:  10927 
    Suche in Google Scholar
  • 1h Grushin VV. Chem. Soc. Rev.  2000,  29:  315 
    Suche in Google Scholar
  • 2a Varvoglis A. Hypervalent Iodine in Organic Synthesis   Academic Press; Oxford: 1997. 
  • 2b Wirth T. Hirt UH. Synthesis  1999,  1271 
  • 2c Zhdankin VV. Stang PJ. Chem. Rev.  2008,  108:  5299 
    Suche in Google Scholar
  • 2d Topics in Current Chemistry   Vol. 224:  Wirth T. Springer; Berlin: 2003. 
  • 3a Boye AC. Meyer D. Ingison CK. French AN. Wirth T. Org. Lett.  2003,  5:  2157 
    Suche in Google Scholar
  • 3b Shah M. Taschner MJ. Koser GF. Rach NL. Tetrahedron Lett.  1986,  27:  4557 
    Suche in Google Scholar
  • 3c Koser GF. Lodaya JS. Ray DG. Kokil PB. J. Am. Chem. Soc.  1988,  110:  2987 
    Suche in Google Scholar
  • 4a Moriarty RM. Vaid RK. Koser GF. Synlett  1990,  365 
  • 4b Koser GF. Aldrichimica Acta  2001,  34:  89 
    Suche in Google Scholar
  • 4c Koser GF. Wettach RH. Smith CS. J. Org. Chem.  1980,  45:  1543 
    Suche in Google Scholar
  • 4d Moriarty RM. Vaid RK. Duncan MP. Levy SG. Prakash O. Goyal S. Synthesis  1992,  845 
  • 4e Prakash O. Goyal S. Synthesis  1992,  629 
  • 4f Prakash O. Saini N. Sharma PK. Synlett  1994,  221 
  • 4g Lee JC. Choi JH. Synlett  2001,  234 
  • 4h Koser GF. Relenyi AG. Kalos AN. Rebrovic L. Wettach RH. J. Org. Chem.  1982,  47:  2487 
    Suche in Google Scholar
  • 5a Dohi T. Kita Y. Kagaku (Kyoto)  2006,  61:  68 
    Suche in Google Scholar
  • 5b Richardson RD. Wirth T. Angew. Chem. Int. Ed.  2006,  45:  4402 
    Suche in Google Scholar
  • 5c Dohi T. Minamitsuji Y. Maruyama A. Hirose S. Kita Y. Org. Lett.  2008,  10:  3559 
    Suche in Google Scholar
  • 5d Ochiai M. Chem. Rec.  2007,  7:  13 
    Suche in Google Scholar
  • 5e Uyanik M. Ishihara K. Chem. Commun.  2009,  2086 
  • 5f Dohi T. Kita Y. Chem. Commun.  2009,  2073 
  • 5g Liu H.-G. Tan C.-H. Tetrahedron Lett.  2007,  48:  8220 
    Suche in Google Scholar
  • 6a Yamamoto Y. Togo H. Synlett  2006,  798 
  • 6b Yamamoto Y. Kawano Y. Toy PH. Togo H. Tetrahedron  2007,  63:  4680 
    Suche in Google Scholar
  • 6c Akiike J. Yamamoto Y. Togo H. Synlett  2007,  2168 
  • 6d Moroda A. Togo H. Synthesis  2008,  1257 
  • 6e Ishiwata Y. Togo H. Tetrahedron Lett.  2009,  50:  5354 
    Suche in Google Scholar
  • 6f Suzuki Y. Togo H. Synthesis  2010,  2355 
  • 6g Kawano Y. Togo H. Tetrahedron  2009,  65:  6251 
    Suche in Google Scholar
  • 6h Tanaka A. Togo H. Synlett  2009,  3360 
  • 7 Tanaka A. Moriyama K. Togo H. Synlett  2011,  1853 
  • 8a Merritt EA. Carneiro VMT. Silva LF. Olofsson B. J. Org. Chem.  2010,  75:  7416 
    Suche in Google Scholar
  • 8b Zhu M. Jalalian N. Olofsson B. Synlett  2008,  592 
  • 8c Bielawski M. Olofsson B. Chem. Commun.  2007,  2521 
  • 8d Bielawski M. Zhu M. Olofsson B. Adv. Synth. Catal.  2007,  349:  2610 
    Suche in Google Scholar
  • 9a Uyanik M. Okamoto H. Yasui T. Ishihara K. Science (Washington, D.C.)  2010,  328:  1376 
    Suche in Google Scholar
  • 9b Krishna Mohan KVV. Narender N. Kulkarni SJ. Tetrahedron Lett.  2004,  45:  8015 
    Suche in Google Scholar
  • 10 Sakurai N. Mukaiyama T. Chem. Lett.  2008,  37:  388 
    Suche in Google Scholar
  • 11 Khanna MS. Garg CP. Kapoor RP. Tetrahedron Lett.  1992,  33:  1495 
    Suche in Google Scholar
  • 12 Su F. Zhang JZ. Jin GY. Qiu T. Zhao DJ. Jia HB. J. Chem. Res.  2009,  741 
  • 13 Hodson D. Holt G. Wall DK. J. Chem. Soc. C  1970,  971 
  • 14 Altermann SM. Richardson RD. Page TK. Schmidt RK. Holland E. Mohammed U. Paradine SM. French AN. Richter C. Bahar AM. Witulski B. Wirth T. Eur. J. Org. Chem.  2008,  5315 
  • 15 John ORS. Killeen NM. Knowles DA. Yau SC. Bagle MC. Tomkinson NCO. Org. Lett.  2007,  9:  4009 
    Suche in Google Scholar
  • 16 Moriarty RM. Penmasta R. Awasthi AK. Epa WR. Prakash I. J. Org. Chem.  1989,  54:  1101 
    Suche in Google Scholar
  • 17 Mahajan US. Akamanchi KG. Synlett  2008,  987 
  • 18 Hatzigrigoriou E. Varvoglis A. Bakola-Christianopoulou M. J. Org. Chem.  1990,  55:  315 
    Suche in Google Scholar