Synthesis 2005(20): 3499-3501  
DOI: 10.1055/s-2005-918492
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

Deoxygenation of Sulfoxide and Aza-aromatic N-Oxide Using a Protocol of Indium and Acyl Chloride

Eun Soo Parka, Seung Hwan Leea, Ji Hee Leea, Hak June Rheeb, Cheol Min Yoon*c
a Graduate School of Biotechnology, Korea University, Sungbuk-ku Anamdong 5, 1 ga, 136-701 Seoul, South Korea
b College of Science and Technology, Hanyang University, Sangnok-ku Sa-1 dong 1271, 425-791 Kyeonggi-do, South Korea
c Department of Advanced Material Chemistry, Korea University, Jochiwon, 339-800 Choongnam, South Korea
Fax: +82(2)32903433; e-Mail: cmyoon@korea.ac.kr;
Further Information

Publication History

Received 17 February 2005
Publication Date:
24 November 2005 (eFirst)

Abstract

Sulfoxides and aza-aromatic N-oxides were deoxygenated using a system of indium and pivaloyl chloride at room temperature to give the corresponding sulfides and aza-aromatics in high yields.

    References

  • 1a Carreno MC. Chem. Rev.  1995,  95:  1717 
  • 1b Solladie G. Antonio A. Dominguez C. Pure Appl. Chem.  1994,  66:  2159 
  • 1c Walker AJ. Tetrahedron: Asymmetry  1992,  3:  961 
  • 2 Madesclaire M. Tetrahedron  1988,  44:  6537 
  • 3a Bhatia GS. Graczyk PP. Tetrahedron Lett.  2004,  45:  5193 
  • 3b Harrison DJ. Tam NC. Vogels CM. Langler RF. Baker RT. Decken RT. Stephen A. Westcott SA. Tetrahedron Lett.  2004,  45:  8493 
  • 4a Kukushkin VY. Coord. Chem. Rev.  1990,  59:  844 
  • 4b Kukushkin VY. Russ. Chem. Rev.  1990,  59:  844 
  • 4c Drabowicz J. Numata T. Oae S. Org. Prep. Proced. Int.  1977,  9:  63 
  • 5a Podlech J. Maier TC. Synthesis  2003,  633 
  • 5b Pitts MR. Harrison JR. Moody CJ. J. Chem. Soc., Perkin Trans. 1  2001,  955 
  • 5c Ranu BC. Eur. J. Org. Chem.  2000,  2347 
  • 5d Li CJ. Chan TH. Tetrahedron  1999,  55:  11149 
  • 5e Loh TP. Hu QY. Vittal JJ. Synlett  2000,  523 
  • 5f Loh TP. Zhou JR. Li XR. Tetrahedron Lett.  1999,  40:  9333 
  • 6a Abrovitch RA. Saha JG. Adv. Heterocycl. Chem.  1966,  6:  229 
  • 6b Grimmett MR. Adv. Heterocycl. Chem.  1993,  58:  271 
  • 6c Morimoto Y. Kurihara H. Yokoe C. Kinoshita T. Chem. Lett.  1989,  829 
  • 6d Yadav JS. Subba Reddy BV. Muralidhar Reddy M. Tetrahedron Lett.  2000,  41:  2663 
  • 7 Yadav JS. Subba Reddy BV. Muralidhar Reddy M. Tetrahedron Lett.  2000,  41:  2663 
  • 8 Yoo BW. Choi JW. Kim DY. Hwang SK. Choi KI. Kim JH. Bull. Korean Chem. Soc.  2002,  23:  797 
  • 9 Lee SH. Park YS. Nam MH. Yoon CM. Org. Biomol. Chem.  2004,  2:  2170 
  • 10 Nicolaou KC. Koumbis AE. Angew. Chem. Int. Ed.  2000,  39:  2529 
  • 11 Yadav JS. Reddy BVS. Reddy GSKK. New J. Chem.  2000,  24:  571 
  • 12 Bur SK. Padwa A. Chem. Rev.  2004,  104:  2401 
  • 13 Ranu BC. Dutta P. Sarkar A. Tetrahedron Lett.  1998,  39:  9557 
  • 14 Oxygenation of sulfoxides to sulfides: Ranu BC. Dutta P. Sarkar A. J. Chem. Soc., Perkin Trans. 1  1999,  1139 
  • 15 Sanz R. Escribano J. Aguado R. Pedrosa MR. Arnáiz FJ. Synthesis  2004,  1629 
  • 16a Nasser I. Habib F. Hamid RS. J. Org. Chem.  2002,  67:  2826 
  • 16b Marques A. Marin M. Ruasse M.-F. J. Org. Chem.  2001,  66:  7588 
  • 16c Kim SS. Rajagopal G. Synthesis  2003,  2461 
  • 17a Shuman RT. Ornstein PL. Paschal JW. Gesellchen PD. J. Org. Chem.  1990,  55:  738 
  • 17b Jain SL. Sain B. Angew. Chem. Int. Ed.  2003,  42:  1265 
  • 17c Brougham P. Cooper MS. Cummerson DA. Heaney H. Thompson N. Synthesis  1987,  1 
  • 17d Lohse O. Lohse O. Thevenin P. Waldvogel E. Synlett  1999,  45 
  • 18a Metzner P. Thuillier A. In Sulfur Reagents in Organic Synthesis   Academic Press; London: 1994. 
  • 18b Xu WL. Li YZ. Zhang QS. Zhu HS. Synthesis  2004,  227 
  • 19 Shuman RT. Ornstein PL. Paschal JW. Gesellchen PD. J. Org. Chem.  1990,  55:  738