Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2002(4): 0479-0482
DOI: 10.1055/s-2002-20958
DOI: 10.1055/s-2002-20958
PAPER
© Georg Thieme Verlag Stuttgart · New York
One-Pot Synthesis of Aryl Sulfones from Alcohols
Further Information
Received
18 December 2001
Publication Date:
28 July 2004 (online)
Publication History
Publication Date:
28 July 2004 (online)
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.
Key words
sulfones - alcohols - sulfinates - one-pot synthesis
- 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