Synlett 2012; 23(18): 2615-2618
DOI: 10.1055/s-0032-1317343
letter
© Georg Thieme Verlag Stuttgart · New York

Woollins Reagent: A Chemoselective Reducing Agent for 1,4-Enediones and 1,4-Ynediones to Saturated 1,4-Diones

Madhumita Mandal
Department of Chemistry, CSIR-Indian Institute of Chemical Biology, 4, Raja S. C. Mullick Road, Calcutta 700032, India   Fax: +91(33)24735197   Email: jaisankar@iicb.res.in
,
Sourav Chatterjee
Department of Chemistry, CSIR-Indian Institute of Chemical Biology, 4, Raja S. C. Mullick Road, Calcutta 700032, India   Fax: +91(33)24735197   Email: jaisankar@iicb.res.in
,
Parasuraman Jaisankar*
Department of Chemistry, CSIR-Indian Institute of Chemical Biology, 4, Raja S. C. Mullick Road, Calcutta 700032, India   Fax: +91(33)24735197   Email: jaisankar@iicb.res.in
› Author Affiliations
Further Information

Publication History

Received: 12 July 2012

Accepted after revision: 10 September 2012

Publication Date:
12 October 2012 (online)


Abstract

Woollins reagent was found to act as a highly chemo­selective reagent for the reduction of a wide range of 1,4-enediones and 1,4-ynediones in methanol to afford the corresponding saturated 1,4-diketones in good yields under mild reaction conditions.

Supporting Information

 
  • References

  • 1 Ismail KA, El-Tombary AA, Aboulwafa OM, Omar AM. M. E, El-Rewini SH. Arch. Pharm. Pharm. Med. Chem. 1996; 329: 433
  • 2 Finch N, Fitt JJ, Hsu IH. C. J. Org. Chem. 1971; 36: 3191
  • 3 Bergman R, Nilsson B, Wickberg B. Tetrahedron Lett. 1990; 31: 2783
  • 4 Lu X, Ji J, Ma D, Shen W. J. Org. Chem. 1991; 56: 5774
  • 5 Sul’man EM. Russ. Chem. Rev. 1994; 63: 923
  • 6 Power MB, Barron AR. Tetrahedron Lett. 1990; 31: 323
  • 7 Gallezot P, Richard D. Catal. Rev.: Sci. Eng. 1998; 40: 81
  • 8 Arai M, Takahashi H, Shirai M, Nishiyama Y, Ebina T. Appl. Catal. A. 1999; 176: 229
  • 9 Singh UK, Vannice MA. J. Catal. 2000; 191: 165
  • 10 Shirai M, Tanaka T, Arai M. J. Mol. Catal. A 2001; 168: 99
  • 11 Ando C, Kurokawa H, Miura H. Appl. Catal. A 1999; 185: 181
  • 12 Salman F, Park C, Baker RT. K. Catal. Today 1999; 53: 385
  • 13 Coloma F, Llorca J, Homs N, de la Piscina PR, Rodríguez-Reinoso F, Sepúlveda-Escribano A. Phys. Chem. Chem. Phys. 2000; 2: 3063
  • 14 Bachiller-Baeza B, Rodríguez-Ramos I, Guerrero-Ruiz A. Appl. Catal. A 2001; 205: 227
  • 15 Doi T, Fukuyama T, Horiguchi J, Okamura T, Ryu I. Synlett 2006; 721
  • 16 Bhattacharyya P, Woollins JD. Tetrahedron Lett. 2001; 42: 5949
  • 17 Hua G, Woollins JD. Angew. Chem. Int. Ed. 2009; 48: 1368
  • 18 Gray IP, Bhattacharyya P, Slawin AM. Z, Woollins JD. Chem.–Eur. J. 2005; 11: 6221
  • 19 Hua G, Griffin JM, Ashbrook SE, Slawin AM. Z, Woollins JD. Angew. Chem. Int. Ed. 2011; 50: 4123
  • 20 Woollins JD. Synlett 2012; 23: 1154
  • 21 Fitzmaurice JC, Williams DJ, Wood PT, Woollins JD. J. Chem. Soc., Chem Commun. 1988; 741
  • 22 Hua G, Li Y, Slawin AM. Z, Woollins JD. Dalton Trans. 2007; 1477
  • 23 Bethke J, Karaghiosoff K, Wessjohann LA. Tetrahedron Lett. 2003; 44: 6911
  • 24 Bhattacharyya P, Slawin AM. Z, Woollins JD. J. Chem. Soc., Dalton Trans. 2001; 300
  • 25 For the synthesis and spectral data of cis-dibenzoyl ethylene, see: Rappai JP, Prathapan S, Unni MV. V, Unnikrishnan PA. Synth. Commun. 2007; 37: 569
  • 26 For the synthesis and spectral data of 5a, see: Zotto AD, Baratta W, Verardo G, Rigo P. Eur. J. Org. Chem. 2000; 2795
  • 27 For the synthesis and spectral data of 6a, see: Xue S, Li LZ, Liu YK, Guo QX. J. Org. Chem. 2006; 71: 215
  • 28 For the synthesis and spectral data of 5b, see: Runcie KA, Taylor RJ. K. Chem. Commun. 2002; 974
  • 29 For spectral data of 6b, see: Bortolini O, Fantin G, Fogagnolo M, Giovannini PP, Massi A, Pacifico S. Org. Biomol. Chem. 2011; 9: 8437
  • 30 For spectral data of 2b, see: Nishiyama Y, Kobayashi A. Tetrahedron Lett. 2006; 47: 5565
  • 31 For spectral data of 2c, see: Shohei I, Teruaki M. Chem. Lett. 2007; 36: 78
  • 32 For spectral data of 2d, see: Chacko SA, Wenthold PG. J. Org. Chem. 2007; 72: 494
  • 33 For spectral data of 3ad, see: Jiang H, Zeng W, Li Y, Wu W, Huang L, Fu W. J. Org. Chem. 2012; 77: 5179
  • 34 For spectral data of 7a, see: Imagawa H, Kurisaki T, Nishizawa M. Org. Lett. 2004; 6: 3679
  • 35 For spectral data of 7b, see: Rigo B, Valligny D, Taisne S, Couturier D. Synth. Commun. 1988; 18: 167
    • 36a Hua G, Li Y, Slawin AM. Z, Woollins JD. Eur. J. Inorg. Chem. 2007; 891
    • 36b Hua G, Li Y, Slawin AM. Z, Woollins JD. Chem. Commun. 2007; 1465
  • 37 Dey S, Pal C, Nandi D, Giri VS, Zaidlaweiz M, Krzeminiski M, Smentek L, Hess BA. J, Gawronski J, Kwit M, Babu NJ, Nangia A, Jaisankar P. Org. Lett. 2008; 10: 1373