280
Views
6
CrossRef citations to date
0
Altmetric
SHORT COMMUNICATION

A facile and efficient procedure for the deoxygenation of sulfoxides to sulfides with the HfCl4/Zn system

, &
Pages 358-363 | Received 15 Feb 2015, Accepted 15 Mar 2015, Published online: 24 Apr 2015

References

  • Firouzabadi H, Jamalian A. Reduction of oxygenated organosulfur compounds. J Sulfur Chem. 2008;29:53–97. doi: 10.1080/17415990701684776
  • Carreno MC. Applications of sulfoxides to asymmetric synthesis of biologically active compounds. Chem Rev. 1995;95:1717–1760. doi: 10.1021/cr00038a002
  • Volonterio A, Bravo O, Pesenti C, Zanda M. The ‘non-oxidative’ chloro-Pummerer reaction: a highly stereoselective entry to β-chloro amines and aziridines. Tetrahedron Lett. 2001;42:3985–3988. doi: 10.1016/S0040-4039(01)00651-7
  • Solladie G. In: Morrison JD, editor. Asymmetric synthesis. New York: Academic; 1983; Vol. 2, p. 157–199.
  • Walker AJ. Asymmetric carbon–carbon bond formation using sulfoxide-stabilised carbanions. Tetrahedron Asymmetry. 1992;3:961–998. doi: 10.1016/S0957-4166(00)86026-7
  • Schmizu M, Shibuya K, Hayakawa R. Chemoselective deoxygenation of sulfoxides with titanium tetraiodide. Synlett. 2000;11:1437–1438.
  • Khurana JM. Deoxygenation of sulfoxides and selenoxides with nickel boride. Tetrahedron Lett. 1998;39:3829–3832. doi: 10.1016/S0040-4039(98)00623-6
  • Yadav JS, Reddy BVS, Srinivas C, Srihari P. Ultrasound-promoted deoxygenation of sulfoxides by samarium-NH4Cl. Synlett. 2001;12:854–856. doi: 10.1055/s-2001-14911
  • Balicki R. Mild and efficient deoxygenation of sulfoxides with titanium(IV) chloride/sodium iodide reagent system. Synthesis. 1991;2:155–156. doi: 10.1055/s-1991-26402
  • Miller SJ, Collier TR, Wu W. Efficient reduction of sulfoxides with 2,6-dihydroxypyridine. Tetrahedron Lett. 2000;41:3781–3783. doi: 10.1016/S0040-4039(00)00502-5
  • Khurana JM, Sharma V, Chacko SA. Deoxygenation of sulfoxides, selenoxides, telluroxides, sulfones, selenones and tellurones with Mg-MeOH. Tetrahedron. 2007;63:966–969. doi: 10.1016/j.tet.2006.11.027
  • Bhatia GS, Graczyk PP. A mild protocol for the deoxygenation of α-hydrogen-containing sulfoxides to the corresponding sulfoxides to the corresponding sulfides. Tetrahedron Lett. 2004;45:5193–5195. doi: 10.1016/j.tetlet.2004.05.049
  • Hua G, Woolin JD. The synthesis of sulfides by deoxygenation of sulfoxides using Woollins’ reagent. Tetrahedron Lett. 2007;48:3677–3679. doi: 10.1016/j.tetlet.2007.03.132
  • Cabrita I, Sousa SCA, Fernandes AC. Reduction of sulfoxides catalyzed by oxo-complexes. Tetrahedron Lett. 2010;51:6132–6135. doi: 10.1016/j.tetlet.2010.09.071
  • Sousa SCA, Bernardo JR, Romao CC, Fernandes, AC. Highly efficient rhenium-catalyzed deoxygenation of sulfoxides without adding any reducing agent. Tetrahedron. 2012;68:8194–8197. doi: 10.1016/j.tet.2012.07.071
  • Bahrami K, Khodaei MM, Karimi A. Mild and efficient deoxygenation of sulfoxides to sulfides with triflic anhydride/potassium iodide reagent system. Synthesis. 2008;16:2543–2546. doi: 10.1055/s-2008-1067190
  • Guidon Y, Atkinson JG, Morton HE. Deoxygenation of sulfoxides with boron bromide reagents. J Org Chem. 1984;49:4538–4540. doi: 10.1021/jo00197a043
  • Bahrami K, Khodaei MM, Khedri M. A novel method for the deoxygenation of sulfoxides with the PPh3/Br2/CuBr system. Chem Lett. 2007;36:1324–1325. doi: 10.1246/cl.2007.1324
  • Cintas P. Activated Metals in Organic Synthesis. Boca Raton, FL: CRC; 1993.
  • Yoo BW, Song MS, Park CM. Mild and efficient deoxygenation of sulfoxides with MoCl5/indium system. Synth Commun. 2007;37:3089–3093. doi: 10.1080/00397910701544729
  • Habib F, Babak K. Efficient deoxygenation of sulfoxides to thioethers and reductive coupling of sulfonyl chlorides to disulfides with tungsten hexachloride. Synthesis. 1999;31:500–502.
  • Wang JQ, Zhang YM. Facile and mild reduction of sulfoxides to sulfides with TiCl4/Sm system. Synth. Commun. 1995;25:3545–3547. doi: 10.1080/00397919508015489
  • Han JH, Choi JW, Choi KI, Kim JH, Yoo BW. A facile and efficient reductionof nitroarenes with NiCl2 6H2O/indium system. Bull Korean Chem Soc. 2006;27:1115–1116. doi: 10.5012/bkcs.2006.27.8.1115
  • Yoo BW, Choi JW. Mild and efficient deoxygenation of amine-N-oxides with BiCl3/indium system. Synth Commun. 2009;39:3550–3554. doi: 10.1080/00397910902788190
  • Yoo BW, Kim SH, Kim JH. A mild, efficient, and selective debromination of vic-dibromides to alkenes with Cp2TiCl2/Ga system. Bull Korean Chem Soc. 2010;31:2757–2758. doi: 10.5012/bkcs.2010.31.10.2757
  • Yoo BW, Park MC, Shin JI. Rapid and mild deoxgenation of sulfoxides with MoCl5/gallium system under sonication. Bull Korean Chem Soc. 2009;30:1927–1928. doi: 10.5012/bkcs.2009.30.9.1927
  • Naoki A, Jian-Xiu L, Tomoko S, Yoshinori Y. Lewis acid-catalyzed hydrostannation of acetylenes. regio- and stereoselective trans-addition of tributyltin hydride and dibutyltin dihydride. J Org Chem. 1996;61:4568–4571. doi: 10.1021/jo952273w
  • Kazuaki I, Masaya N, Suguru O, Hisashi Y. Direct ester condensation from a 1:1 mixture of carboxylic acids and alcohols catalyzed by hafnium(IV) or zirconium(IV) salts. Tetrahedron. 2002;58:8179–8188. doi: 10.1016/S0040-4020(02)00966-3
  • Jiangghua Z, Xinqin G, Chengyi Z, Cheng Z, Jiming L, Defeng Z. Mild and efficient deoxygenation of sulfoxides to sulfides using HfCl4/KBH4 system. Synth Commun. 2010;40:1794–1801. doi: 10.1080/00397910903161819
  • Nicolaou KC, Koumbis AE, Snyder SA, Simonsen KB. Novel reduction initiated by titanocene methylidenes: deoxygenation of sulfoxides, N-oxides, and selenoxides. Angew Chem Int Ed. 2000;39:2529–2533. doi: 10.1002/1521-3773(20000717)39:14<2529::AID-ANIE2529>3.0.CO;2-E
  • Alper H, Keung ECH. Deoxygenation of sulfoxides by iron pentacarbonyl. Tetrahedron Lett. 1970;11:53–56. doi: 10.1016/S0040-4039(01)87563-8
  • Chasar DW. Quantitative reduction of sulfoxides. J Org Chem. 1971;36:613–614. doi: 10.1021/jo00803a033
  • Oh KS, William EK. Lewis acid-promoted electron transfer deoxygenation of epoxides, sulfoxides, and amine N-oxides: the role of low-valent niobium complexes from NbCl5 and Zn. Tetrahedron. 2009;65:2966–2974. doi: 10.1016/j.tet.2009.02.013
  • Pouchert CJ, Behnke J, editors. The Aldrich Library of 13C and 1H FT-NMR spectra. Aldrich: Milwaukee; 1992.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.