B(C₆F₅)₃-Catalyzed Reduction of Sulfoxides and Sulfones to Sulfides with Hydrosilanes

Abstract

B(C₆F₅)₃ is shown to catalyze the deoxygenation of sulfoxides and sulfones to the corresponding sulfides with Et₃SiH as the stoichiometric hydride source. While the method is limited in terms of functional group tolerance, it is applicable to the reduction of alkyl/aryl-, aryl/aryl-, and alkyl/alkyl-substituted sulfoxides, including the benzyl/benzyl-substituted derivative. The same protocol converts alkyl/aryl- but not aryl/aryl-substituted sulfones into sulfides.

Key words

boron - Lewis acids - reduction - Si–H activation - silicon

• References and Notes

• 1a Kunieda N. Nokami J. Kinoshita M. Chem. Lett. 1974; 369
• 1b Solladié G. Synthesis 1981; 185
• 1c Kosugi H. Konta H. Uda H. J. Chem. Soc., Chem. Commun. 1985; 211
• 1d Solladié G. Demailly G. Greck C. Tetrahedron Lett. 1985; 26: 435
• 1e Kosugi H. Watanabe Y. Uda H. Chem. Lett. 1989; 1865
• 2a Carreno MC. Chem. Rev. 1995; 95: 1717
• 2b Madesclaire M. Tetrahedron 1988; 44: 6537
• 3 Magnus PD. Tetrahedron 1977; 33: 2019
• 4 Desrosiers JN. Charette AB. Angew. Chem. Int. Ed. 2007; 46: 5955
• 5a Zhu Z. Espenson JH. J. Mol. Catal. A: Chem. 1995; 103: 87
• 5b Arterburn JB. Perry MC. Tetrahedron Lett. 1996; 37: 7941
• 5c Sanz R. Escribano J. Aguado RM. Pedrosa R. Arnáiz FJ. Synthesis 2004; 1629
• 5d Bagherzadeh M. Haghdoost MM. Amini M. Derakhshandeh PG. Catal. Commun. 2012; 23: 14
• 6a Sousa SC. A. Fernandes AC. Tetrahedron Lett. 2009; 50: 6872
• 6b Fernandes AC. Romão CC. Tetrahedron 2006; 62: 9650
• 6c Cabrita I. Sousa SC. A. Fernandes AC. Tetrahedron Lett. 2010; 51: 6132
• 6d Enthaler S. Catal. Sci. Technol. 2011; 1: 104
• 6e Enthaler S. ChemCatChem 2011; 3: 666
• 6f Krackl S. Company A. Enthaler S. Driess M. ChemCatChem 2011; 3: 1186
• 6g Enthaler S. Weidauer M. Catal. Lett. 2011; 141: 833
• 6h Mikami Y. Noujima A. Mitsudome T. Mizugaki T. Jitsukawa K. Kaneda K. Chem. Eur. J. 2011; 17: 1768
• 6i Thiel K. Zehbe R. Roeser J. Strauch P. Enthaler S. Thomas A. Polym. Chem. 2013; 4: 1848
• 7a Fernandes AC. Romão CC. Tetrahedron Lett. 2007; 48: 9176
• 7b Enthaler S. Krackl S. Irran E. Inoue S. Catal. Lett. 2012; 142: 1003
• 7c Enthaler S. Catal. Lett. 2012; 142: 1306
• 8a Wallace TJ. Mahon JJ. J. Am. Chem. Soc. 1964; 86: 4099
• 8b Karimi B. Zareyee D. Synthesis 2003; 1875
• 9a Chasar DW. J. Org. Chem. 1971; 36: 613
• 9b Drabowicz J. Mikolajczyk M. Synthesis 1976; 527
• 9c Kano S. Tanaka Y. Sugino E. Hibino S. Synthesis 1980; 695
• 9d Harrison DJ. Tam NC. Vogels CM. Langler RF. Baker RT. Decken A. Westcott SA. Tetrahedron Lett. 2004; 45: 8493
• 9e Zhang J. Gao X. Zhang C. Luan J. Zhao D. Synth. Commun. 2010; 40: 1794
• 10 Iranpoor N. Firouzabadi H. Shaterian HR. J. Org. Chem. 2002; 67: 2826
• 11a Gazdar M. Smiles S. J. Chem. Soc. 1910; 97: 2248
• 11b Aida T. Furukawa N. Oae S. Tetrahedron Lett. 1973; 14: 3853
• 11c Landini D. Maia AM. Rolla F. J. Chem. Soc., Perkin Trans. 2 1976; 1288
• 11d Doi JT. Musker WK. J. Am. Chem. Soc. 1981; 103: 1159
• 12a Castrillón JP. A. Szmant HH. J. Org. Chem. 1965; 30: 1338
• 12b Still IW. J. Hasan SK. Turnbull K. Can. J. Chem. 1978; 56: 1423
• 12c Kikuchi S. Konishi H. Hashimoto Y. Tetrahedron 2005; 61: 3587
• 12d Iranpoor N. Firouzabadi H. Jamalian A. Synlett 2005; 1447
• 12e Hua G. Woollins JD. Tetrahedron Lett. 2007; 48: 3677
• 12f Bahrami K. Khodaei MM. Khedri M. Chem. Lett. 2007; 36: 1324
• 12g Pandey LK. Pathak U. Rao AN. Synth. Commun. 2007; 37: 4105
• 12h Jang Y. Kim KT. Jeon HB. J. Org. Chem. 2013; 78: 6328
• 13 Akgün E. Mahmood K. Mathis CA. J. Chem. Soc., Chem. Commun. 1994; 761
• 14a Whitney TA. Cram DJ. J. Org. Chem. 1970; 35: 3964
• 14b Weber WP. Stromquist P. Ito TS. Tetrahedron Lett. 1974; 15: 2595
• 15 Gardner JN. Kaiser S. Krubiner A. Lucas H. Can. J. Chem. 1973; 51: 1419
• 16 Bordwell FG. McKellin WH. J. Am. Chem. Soc. 1951; 73: 2251
• 17 Oae S. Kawamura S. Bull. Chem. Soc. Jpn. 1963; 36: 163
• 18 While this manuscript was in preparation, Shi and co-workers reported the same B(C₆F₅)₃-catalyzed sulfoxide reduction. Ding F. Jiang Y. Gan S. Bao RL.-Y. Kaifeng L. Shi L. Eur. J. Org. Chem. 2017; 3427
• 19 For a recent summary, see: Oestreich M. Hermeke J. Mohr J. Chem. Soc. Rev. 2015; 44: 2202
• 20 Mehta M. Garcia de la Arada I. Perez M. Porwal D. Oestreich M. Stephan DW. Organometallics 2016; 35: 1030
• 21 Porwal D. Oestreich M. Eur. J. Org. Chem. 2016; 3307
• 22a Ma R. Liu A.-H. Huang C.-B. Li X.-D. He L.-N. Green Chem. 2013; 15: 1274
• 22b Firouzabadi H. Iranpoor N. Gorginpour F. Samadi A. Eur. J. Org. Chem. 2015; 2914