One-Pot Synthesis of Aryl Sulfones from Alcohols

Abstract

A one-pot synthesis of aryl sulfones from primary alcohols is described. Alcohols were treated with N-bromosuccinimide and triphenylphosphine, followed by addition of sodium arenesulfinate with a catalytic amount of tetrabutylammonium iodide to afford the aryl sulfones in good to high yields.

sulfones - alcohols - sulfinates - one-pot synthesis

References

For reviews, see:

1a Trost BM. Bull. Chem. Soc. Jpn.  1988,  61:  107 

1b Solladie G. In Comprehensive Organic Synthesis   Vol. 6:  Trost BM. Fleming I. Pergamon Press; Oxford: 1991.  p.157 

1c Simpkins NS. In Sulphones in Organic Synthesis   Pergamon Press; Oxford: 1993. 

1d Nájera C. Yus M. Tetrahedron  1999,  55:  10547 

1e Procter DJ. J. Chem. Soc., Perkin Trans. 1  2000,  835 

2a Orita A. Yamashita Y. Toh A. Otera J. Angew. Chem., Int. Ed. Engl.  1997,  36:  779 

2b Lipshutz BH. Bulow G. Fernandez-Lazaro F. Kim S.-K. Lowe R. Molar P. Stevens KL. J. Am. Chem. Soc.  1999,  121:  11664 

3a Julia M. Righini A. Verpeaux J.-N. Tetrahedron Lett.  1979,  2393 

3b Trost BM. Schmuff NR. Miller MJ. J. Am. Chem. Soc.  1980,  102:  5979 

3c Trost BM. Ghadiri MR. J. Am. Chem. Soc.  1986,  108:  1098 

4a Clayden J. Julia M. J. Chem. Soc., Chem. Commun.  1994,  1905 

4b Clayden J. Julia M. J. Chem. Soc., Chem. Commun.  1994,  2261 

5a Smith TAK. Whitham GH. J. Chem. Soc., Perkin Trans. 1  1989,  313 

5b Padwa A. Bullock WH. Dyszlewski AD. J. Org. Chem.  1990,  55:  955 

5c Pontén F. Magnusson G. J. Org. Chem.  1996,  61:  7463 

6 Trost BM. Schmuff NR. J. Am. Chem. Soc.  1985,  107:  396 ; and references cited therein

7a Trost BM. Braslau R. J. Org. Chem.  1988,  53:  532 

7b Sato K. Hyodo M. Aoki M. Zheng X.-Q. Noyori R. Tetrahedron  2001,  57:  2469 

8a Julia M. Nel M. Saussine L. J. Organomet. Chem.  1979,  181:  C17 

8b Inomata K. Yamamoto T. Kotake H. Chem. Lett.  1981,  1357 

9a Boldrini GP. Savoia D. Tagliavini E. Trombini C. Umani-Ronchi A. J. Organomet. Chem.  1984,  268:  97 

9b Ono N. Hamamoto I. Kawai T. Kaji A. Tamura R. Kakihana M. Bull. Chem. Soc. Jpn.  1986,  59:  405 

10a Manchand PS. Rosenberger M. Saucy G. Wehrli PA. Wong H. Chambers L. Ferro MP. Jackson W. Helv. Chim. Acta  1976,  59:  387 

10c Kanai T. Kanagawa Y. Ishii Y. J. Org. Chem.  1990,  55:  3274 

11 Murakami T. Shimizu T. Taguchi K. Tetrahedron  2000,  56:  533 

12 Collington EW. Meyers AI. J. Org. Chem.  1971,  36:  3044 

To increase the solubility of arenesulfinate salts in common organic solvents, phase transfer catalysts such as Bu₄NI are often employed, see:

13a Wildeman J. van Leusen AM. Synthesis  1979,  733 

13b Crandall JK. Pradat C. J. Org. Chem.  1985,  50:  1327 

14 Meek JS. Fowler JS. J. Org. Chem.  1968,  33:  3422 

15 For a review: Castro BR. Org. React.  1983,  29:  1 

16 Yamamoto I. Sekine M. Hata T. J. Chem. Soc., Perkin Trans. 1  1980,  306 

17 Mizuno A. Hamada Y. Shioiri T. Synthesis  1980,  1007 

18 Frøyen P. Juvvik P. Tetrahedron Lett.  1995,  36:  9555 

19 Bandgar BP. Sadavarte VS. Synlett  2000,  908 

20 In refs. 18 and 19, the authors assumed that the intermediate alkoxyphosphonium bromides directly reacted with a nucleophile to give the final products. In our cases, however, rapid formation of alkyl bromides and triphenyphosphine oxide was observed by TLC and NMR analysis before addition of ArSO₂Na, see: Bose AK. Lal B. Tetrahedron Lett.  1973,  3937 

21 Díez Martin D. San Feliciano SG. Marcos IS. Basabe P. Garrido NM. Urones JG. Synthesis  2001,  1069 

22 Li H. Wang H. Pan Y. Shi Y. Synth. Commun.  1998,  28:  409 

23 Gupta BD. Roy M. Roy S. Kumar M. Das I. J. Chem. Soc., Perkin Trans. 2  1990,  537 

24a Katritzky AR. Saba A. Patel RC. J. Chem. Soc., Perkin Trans.1  1981,  1492 

24b Baudin J.-E. Julia M. Rolando C. Verpeaux J.-N. Bull. Soc. Chim. Fr.  1987,  493 

25 Kotake H. Inomata K. Kinoshita H. Sakamoto Y. Kaneto Y. Bull. Chem. Soc. Jpn.  1980,  53:  3027 

26 Stirling CJM. J. Chem. Soc.  1964,  5856 

27a Pillot J.-P. Dunogues J. Calas R. Synthesis  1977,  469 

27b King JF. Rathore R. Guo Z. Li M. Payne NC. J. Am. Chem. Soc.  2000,  122:  10308 

28

29 Bell R. Cottam PD. Davies J. Jones DN. J. Chem. Soc., Perkin Trans.1  1981,  2106