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Synthesis 2010(2): 315-319  
DOI: 10.1055/s-0029-1217093
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

o-Benzenedisulfonimide as a Reusable Brønsted Acid Catalyst for Hosomi-Sakurai Reactions

Margherita Barbero, Stefano Bazzi, Silvano Cadamuro, Stefano Dughera*, Claudia Piccinini
Dipartimento di Chimica Generale e Chimica Organica, Università di Torino, C.so Massimo d’Azeglio 48, 10125 Torino, Italy
Fax: +39(011)6707642; e-Mail: stefano.dughera@unito.it;
Further Information

Publication History

Received 3 September 2009
Publication Date:
03 November 2009 (online)

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Abstract

Various acetals or alcohols react with allyl(trimethyl)silane or 1-phenyl-2-(trimethylsilyl)acetylene in the presence of a catalytic amount of the Brønsted acid o-benzenedisulfonimide under mild conditions to give good yields of the corresponding products. The catalyst can be easily recovered and purified for use in further reactions, which has economic and ecological advantages.

Key words

homogeneous catalysis - Brønsted acid - Hosomi-Sakurai­ reaction - acetals - alcohols

    References

  • 1a Barbero M. Cadamuro S. Dughera S. Venturello P. Synlett  2007,  2209 
  • 1b Barbero M. Cadamuro S. Dughera S. Venturello P. Synthesis  2008,  1379 
  • 2 Barbero M. Cadamuro S. Dughera S. Venturello P. Synthesis  2008,  3625 
    Thieme Connect
  • 3 Barbero M. Bazzi S. Cadamuro S. Dughera S. Eur. J. Org. Chem.  2009,  430 
    Crossref
  • 4 Barbero M. Cadamuro S. Deagostino A. Dughera S. Larini P. Occhiato G. Prandi C. Tabasso S. Venturello P. Vulcano R. Synthesis  2009,  2260 
    Thieme Connect
  • 5 Barbero M. Bazzi S. Cadamuro S. Dughera S. Ghigo G. Eur. J. Org. Chem.  2009,  4346 
    Crossref
  • 6a Hosomi A. Sakurai H. Tetrahedron Lett.  1976,  16:  1295 
    Search in Google Scholar
  • 6b Sakurai H. Pure Appl. Chem.  1982,  54:  1 
    Search in Google Scholar
  • 6c Sakurai H. Sasaki K. Hayashi J. Hosomi A. J. Org. Chem.  1984,  49:  2808 
    Search in Google Scholar
  • 6d Sakurai H. Pure Appl. Chem.  1985,  57:  1759 
    Search in Google Scholar
  • 6e Hosomi A. Acc. Chem. Res.  1988,  21:  200 
    Search in Google Scholar
  • For some recent significant examples of the Hosomi-Sakurai reaction, see:
  • 7a Reddy UC. Bondalapati S. Saikia KA. Eur. J. Org. Chem.  2009,  1625 
  • 7b Sabot C. Guerard KC. Canesi S. Chem. Commun.  2009,  2941 
  • 7c Kumar RSC. Reddy GV. Babu KS. Rao JM. Chem. Lett.  2009,  38:  564 
    Search in Google Scholar
  • 7d Sabot C. Commare B. Duceppe M.-A. Nahi S. Guerard KC. Canesi S. Synlett  2008,  3226 
  • 7e Spangenberg T. Airiau E. Thuong MBT. Donnard M. Billet M. Mann A. Synlett  2008,  2859 
  • 7f Xu L.-W. Yang M.-S. Qiu H.-Y. Lai G.-Q. Jiang J.-X. Synth. Commun.  2008,  38:  1011 
    Search in Google Scholar
  • 7g Shizuka M. Snapper ML. Angew. Chem. Int. Ed.  2008,  47:  5049 
    Search in Google Scholar
  • 7h Das B. Damodar K. Saritha D. Chowdhury N. Krishnaiah M. Tetrahedron Lett.  2007,  48:  7930 
    Search in Google Scholar
  • 7i Saito T. Nishimoto Y. Yasuda M. Baba A. J. Org. Chem.  2006,  71:  8516 
    Search in Google Scholar
  • 7j Ollevier T. Li Z. Org. Biomol. Chem.  2006,  4:  4440 
    Search in Google Scholar
  • 7k Sellars JD. Steel PG. Turner MJ. Chem. Commun.  2006,  2385 
  • 7l Kabalka GW. Yao M.-L. Borella S. J. Am. Chem. Soc.  2006,  128:  11320 
    Search in Google Scholar
  • 7m Nishibayashi Y. Shinoda A. Miyake Y. Matsuzawa H. Sato M. Angew. Chem. Int. Ed.  2006,  45:  4835 
    Search in Google Scholar
  • 7n Wadamoto M. Yamamoto Y. J. Am. Chem. Soc.  2005,  127:  14556 
    Search in Google Scholar
  • For some examples, see:
  • 8a Hayashi M. Inubushi A. Mukaiyama T. Bull. Chem. Soc. Jpn.  1988,  61:  4037 
    Search in Google Scholar
  • 8b Yadav JS. Reddy BVS. Sridhar Reddy M. Parimala G. Synthesis  2003,  2390 
  • 8c Sanz R. Martínez A. Alvarez-Gutiérrez JM. Rodríguez F. Eur. J. Org. Chem.  2006,  1383 
  • 9a Kaur G. Kaushik M. Trehan S. Tetrahedron Lett.  1997,  14:  2521 
    Search in Google Scholar
  • 9b Ishihara K. Hasegawa A. Yamamoto H. Angew. Chem. Int. Ed.  2001,  40:  4077 
    Search in Google Scholar
  • 9c Ishihara K. Hiraiwa H. Yamamoto H. Synlett  2001,  1851 
  • 9d Ishihara K. Hasegawa A. Yamamoto H. Synlett  2002,  1299 
  • 9e Kampen D. List B. Synlett  2006,  2589 
  • 9f Kampen D. Ladépêche A. Claßen G. List B. Adv. Synth. Catal.  2008,  350:  962 
    Search in Google Scholar
  • 10a Spafford MJ. Anderson ED. Lacey JR. Palma AC. Mohan RS. Tetrahedron Lett.  2007,  48:  8665 ; and references cited therein
    Search in Google Scholar
  • 10b Olivero S. Perriot R. Dunach E. Baru AR. Bell ED. Mohan RS. Synlett  2006,  2013 
  • 11a Cui Y.-M. Huang Q.-Q. Xu J. Chen L.-L. Li J.-Y. Ye Q.-Z. Li J. Nan F.-J. Bioorg. Med. Chem. Lett.  2005,  15:  4130 
    Search in Google Scholar
  • 11b Jung YH. Kim JD. Arch. Pharm. Res.  2005,  4:  382 
    Search in Google Scholar
  • 12 Bernardon J.-M. inventors; WO  9733856.  ; Chem. Abstr. 1997, 127, 292999
  • 13 De S K. Gibbs RA. Tetrahedron Lett.  2005,  46:  8345 ; and references cited therein
    CrossrefSearch in Google Scholar
  • 14a Wilkinson JA. Rossington SB. Leonard J. Hussain N. Tetrahedron Lett.  2004,  45:  1191 
    Search in Google Scholar
  • 14b Wilkinson JA. Rossington SB. Coe NA. Hirst N. McGown AT. Leonard J. Hussain N. Lett. Drug Des. Discovery  2007,  4:  246 
    Search in Google Scholar
  • 14c Wilkinson JA. Foretia D. Rossington SB. Heagerty A. Leonard J. Hussain N. Austin C. Eur. J. Pharmacol.  2007,  561:  160 
    Search in Google Scholar
  • 14d Zhao X.-L. Chen Y.-J. Liu L. Wang D. Chin. J. Chem.  2007,  25:  1312 
    Search in Google Scholar
  • 15 Barbero M. Crisma M. Degani I. Fochi R. Perracino P. Synthesis  1998,  1171 
    Thieme Connect
  • 16 Meskens FAJ. Synthesis  1981,  501 
    Thieme Connect
  • 17 Csákÿ AG. Máximo M. Plumet J. Rámila A. Tetrahedron Lett.  1999,  40:  6485 
    CrossrefSearch in Google Scholar
  • 18 Torii S. Inokuchi T. Takagishi S. Horike H. Kuroda H. Uneyama K. Bull. Chem. Soc. Jpn.  1987,  60:  2173 
    CrossrefSearch in Google Scholar
  • 19 Maeda H. Shono K. Ohmori H. Chem. Pharm. Bull.  1994,  42:  1808 
    CrossrefSearch in Google Scholar
  • 20 Jung ME. Maderna A. J. Org. Chem.  2004,  69:  7755 
    CrossrefSearch in Google Scholar
  • 21 Mahrwald R. Quint S. Tetrahedron  2000,  56:  7463 
    CrossrefSearch in Google Scholar
  • 22 Yoshizawa K. Shioiri T. Tetrahedron  2007,  63:  6259 
    CrossrefSearch in Google Scholar
  • 23 Podder S. Choudhury J. Roy S. J. Org. Chem.  2007,  72:  3129 
    CrossrefSearch in Google Scholar
  • 24 Okajima M. Soga K. Nokami T. Suga S. Yoshida J. Org. Lett.  2006,  5005 
    Crossref
  • 25 Mayr H. Bug T. Gotta MF. Hering N. Irrgang B. Janker B. Kempf B. Loos R. Ofial AR. Remennikov G. Schimmel H. J. Am. Chem. Soc.  2001,  123:  9500 
    CrossrefSearch in Google Scholar