Rediscovering the Chemistry of Sulfur Dioxide: New Developments in Synthesis and Catalysis

Abstract

The recent development of several sulfur dioxide surrogates has seen a renaissance in its chemistry, with a number of new synthetic methods being reported. This article reviews the reactions of sulfur dioxide and sulfur dioxide surrogates, with an emphasis on recent examples.

1 Introduction

2 Sulfur Dioxide Surrogates

3 Reactions with Organometallic Reagents

4 Pericyclic Reactions

5 Sulfur Dioxide Radical Chemistry

6 Transition-Metal-Catalysed Processes

7 Conclusions

Key words

sulfur dioxide - surrogate - sulfinate - metal catalysis - sulfone - sulfonamide

• References

• 1 Müller H. Sulfur Dioxide. In Ullmann’s Encyclopedia of Industrial Chemistry. Wiley-VCH; Weinheim: 2000
• 2 Burke SD. Sulfur Dioxide. In Encyclopedia of Reagents for Organic Synthesis. Paquette LA. John Wiley & Sons; Weinheim: 1995
• 3 Vogel P, Turks M, Bouchez L, Markovic D, Varela-Alvarez A, Sordo JA. Acc. Chem. Res. 2007; 40: 931
• 4 Pelzer G, Herwig J, Keim W, Goddard R. Russ. Chem. Bull. 1998; 47: 904
• 5 Li W, Li H, Langer P, Beller M, Wu X.-F. Eur. J. Org. Chem. 2014; 3101
• 6 Ye S, Wu J. Chem. Commun. 2012; 48: 10037
• 7 Shavnya A, Coffey SB, Smith AC, Mascitti V. Org. Lett. 2013; 15: 6226
• 8 Kaneko C, Hayashi R, Fujii H, Yamamoto A. Chem. Pharm. Bull. 1978; 26: 3582
• 9 Bisseret P, Blanchard N. Org. Biomol. Chem. 2013; 11: 5393
• 10 Malwal SR, Sriram D, Yogeeswari P, Konkimalla VB, Chakrapani H. J. Med. Chem. 2012; 55: 553
• 11 Malwal SR, Sriram D, Yogeeswari P, Chakrapani H. Bioorg. Med. Chem. Lett. 2012; 22: 3603
• 12 Malwal SR, Gudem M, Hazra A, Chakrapani H. Org. Lett. 2012; 15: 1116
• 13 Byrd WE. Inorg. Chem. 1962; 1: 762
• 14 Oh JJ, LaBarge MS, Matos J, Kampf JW, Hillig KW, Kuczkowski RL. J. Am. Chem. Soc. 1991; 113: 4732
• 15 Wong MW, Wiberg KB. J. Am. Chem. Soc. 1992; 114: 7527
• 16 Santos PS, Lieder R. J. Mol. Struct. 1986; 144: 39
• 17 Defaria DL. A, Santos PS. Magn. Reson. Chem. 1987; 25: 592
• 18 Santos PS, Mello MT. S. J. Mol. Struct. 1988; 178: 121
• 19 Faria DL. A, Santos PS. J. Raman Spectrosc. 1988; 19: 471
• 20 Burg AB. J. Am. Chem. Soc. 1943; 65: 1629
• 21 Grundnes J, Christian SD. J. Am. Chem. Soc. 1968; 90: 2239
• 22 Olah GA, Arvanaghi M, Vankar YD. Synthesis 1980; 660
• 23 Olah GA, Vankar YD. Synthesis 1978; 702
• 24 Olah GA, Vankar YD, Arvanaghi M. Synthesis 1979; 984
• 25 Olah GA, Vankar YD, Fung AP. Synthesis 1979; 59
• 26 Olah GA, Vankar YD, Gupta BG. B. Synthesis 1979; 36
• 27 Nguyen B, Emmett EJ, Willis MC. J. Am. Chem. Soc. 2010; 132: 16372
• 28 Woolven H, Gonzalez-Rodriguez C, Marco I, Thompson AL, Willis MC. Org. Lett. 2011; 13: 4876
• 29 Emmett EJ, Richards-Taylor CS, Nguyen B, Garcia-Rubia A, Hayter BR, Willis MC. Org. Biomol. Chem. 2012; 10: 4007
• 30 Emmett EJ, Hayter BR, Willis MC. Angew. Chem. Int. Ed. 2013; 52: 12679
• 31 Richards-Taylor CS, Blakemore DC, Willis MC. Chem. Sci. 2014; 5: 222
• 32 Deeming AS, Russell CJ, Hennessy AJ, Willis MC. Org. Lett. 2014; 16: 150
• 33 Patai S. The chemistry of sulphinic acids, esters and their derivatives. John Wiley & Sons; Weinheim: 1990
• 34 Wu JP, Emeigh J, Su X.-P. Org. Lett. 2005; 7: 1223
• 35 Marvel CS, Johnson RS. J. Org. Chem. 1948; 13: 822
• 36 Hamada T, Yonemitsu O. Synthesis 1986; 852
• 37 Waldmann C, Schober O, Haufe G, Kopka K. Org. Lett. 2013; 15: 2954
• 38 Rocke BN, Bahnck KB, Herr M, Lavergne S, Mascitti V, Perreault C, Polivkova J, Shavnya A. Org. Lett. 2014; 16: 154
• 39 Young D, Kitching W. Organometallics 1988; 7: 1196
• 40 Baker EB, Sisler HH. J. Am. Chem. Soc. 1953; 75: 5193
• 41 Fong CW, Kitching W. J. Organomet. Chem. 1970; 21: 365
• 42 Meek JS, Fowler JS. J. Org. Chem. 1968; 33: 3422
• 43 Maiti AK, Bhattacharyya P. Tetrahedron 1994; 50: 10483
• 44 Liang S, Zhang R.-Y, Xi L.-X, Chen S.-Y, Yu X.-Q. J. Org. Chem. 2013; 78: 11874
• 45 Still IW. J, Watson ID. G. Synth. Commun. 2001; 31: 1355
• 46 Pandya R, Murashima T, Tedeschi L, Barrett AG. M. J. Org. Chem. 2003; 68: 8274
• 47 Umierski N, Manolikakes G. Org. Lett. 2013; 15: 4972
• 48 Cacchi S, Fabrizi G, Goggiamani A, Parisi LM, Bernini R. J. Org. Chem. 2004; 69: 5608
• 49 Suarez D, Sordo TL, Sordo JA. J. Org. Chem. 1995; 60: 2848
• 50 Fernandez T, Sordo JA, Monnat F, Deguin B, Vogel P. J. Am. Chem. Soc. 1998; 120: 13276
• 51 Fernandez T, Suarez D, Sordo JA, Monnat F, Roversi E, Estrella de Castro A, Schenk K, Vogel P. J. Org. Chem. 1998; 63: 9490
• 52 Roversi E, Monnat F, Vogel P. Helv. Chim. Acta 2002; 85: 733
• 53 Roulet J.-M, Deguin B, Vogel P. J. Am. Chem. Soc. 1994; 116: 3639
• 54 Suarez D, Iglesias E, Sordo TL, Sordo JA. J. Phys. Org. Chem. 1996; 9: 17
• 55 Sugiura Y, Hojo Y, Tamai Y, Tanaka H. J. Am. Chem. Soc. 1976; 98: 2341
• 56 Suarez D, Sordo TL, Sordo JA. J. Am. Chem. Soc. 1994; 116: 763
• 57 Bohen JM, Jouillie MM. J. Org. Chem. 1973; 38: 2652
• 58 Bellus D. Helv. Chim. Acta 1975; 58: 2509
• 59 Dunkin IR, MacDonald JG. J. Chem. Soc., Perkin Trans. 2 1984; 2: 2079
• 60 Deguin B, Roulet J.-M, Vogel P. Tetrahedron Lett. 1997; 38: 6197
• 61 Huang X, Craita C, Vogel P. J. Org. Chem. 2004; 69: 4272
• 62 Exner CJ, Laclef S, Poli F, Turks M, Vogel P. J. Org. Chem. 2011; 76: 840
• 63 Bouchez LC, Dubbaka SR, Turks M, Vogel P. J. Org. Chem. 2004; 69: 6413
• 64 Bouchez LC, Vogel P. Chem. Eur. J. 2005; 11: 4609
• 65 Hoffmann HM. R. Angew. Chem., Int. Ed. Engl. 1969; 8: 556
• 66 Rogic MM, Masilamani D. J. Am. Chem. Soc. 1977; 99: 5219
• 67 Markovic D, Varela-Alvarez A, Sordo JA, Vogel P. J. Am. Chem. Soc. 2006; 128: 7782
• 68 Bouchez L, Vogel P. Synthesis 2002; 225
• 69 Markovic D, Volla CM. R, Vogel P, Varela-Alvarez A, Sordo JA. Chem. Eur. J. 2010; 16: 5969
• 70 Turks M, Lawrence AK, Vogel P. Tetrahedron Lett. 2006; 47: 2783
• 71 Bertrand MP. Org. Prep. Proced. Int. 1994; 26: 257
• 72 Quiclet-Sire B, Zard SZ. J. Am. Chem. Soc. 1996; 118: 1209
• 73 Meerwein H, Dittmar G, Gollner R, Hafner K, Mensch F, Steinfort O. Chem. Ber. 1957; 50: 841
• 74 Yale HL, Sowinski F. J. Org. Chem. 1960; 25: 1824
• 75 Hoffman RV. Org. Synth. 1990; 7: 508
• 76 Hogan PJ, Cox BG. Org. Process Res. Dev. 2009; 875
• 77 Malet-Sanz L, Madrzak J, Ley SV, Baxendale IR. Org. Biomol. Chem. 2010; 8: 5324
• 78 Zheng D, An Y, Li Z, Wu J. Angew. Chem. Int. Ed. 2014; 53: 2451
• 79 Zheng D, Li Z, An Y, Wu J. Chem. Commun. 2014; 50: 8886
• 80 Ye S, Wu J. Chem. Commun. 2012; 48: 7753
• 81 Strohmeier W, Guttenberger JF. Chem. Ber. 1964; 97: 1871
• 82 Klein HS. J. Chem. Soc., Chem. Commun. 1968; 377
• 83 Drent E. US Patent No. 4808697, 1989 ; Eur. Patent Appl. No. EP 220765, 1987.
• 84 Keim W, Herwig J. J. Chem. Soc., Chem. Commun. 1993; 1592
• 85 Dzhemilev UM, Kunakova RV. J. Organomet. Chem. 1993; 455: 1
• 86 Pelzer G, Keim W. J. Mol. Catal. A: Chem. 1999; 139: 235
• 87 Emmett EJ, Hayter BR, Willis MC. Angew. Chem. Int. Ed. 2014; 53 : in press; doi: 10.1002/anie.201404527
• 88 Johnson MW, Bagley SW, Mankad NP, Bergman RG, Mascitti V, Toste FD. Angew. Chem. Int. Ed. 2014; 53: 4404