Exploiting differences in solution vs solid-supported reactivity for the synthesis of sulfonic acid derivatives

Organic Letters

Volumn 1, Issue 13, 1999, Pages 2109-2111

  Hari, Anitha ^a   Miller, Benjamin L ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000858184     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991163z     Document Type: Article

References (27)

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2. Reviewed in the following: Hodge, P. Chem. Soc. Rev. 1997, 26, 417-424.
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15. By analogy to work carried out by Darling and co-workers on the solid-supported synthesis of solid-supported organosilicon protecting groups (Stranix, B. R.; Liu, H. Q.; Darling, G. D. J. Org. Chem. 1997, 62, 6183-6186), we chose silyl linker 1 as our initial target for study. In addition to being structurally similar to previously reported solution-phase protecting groups, attachment of a sulfonyl halide to 1 would presumably allow for fluoride ion-mediated cleavage of the sulfonate. However, despite repeated attempts, we were unable to observe any sulfonate-containing product on loading of the resin with a sulfonyl halide followed by treatment with tetrabutylammonium fluoride (TBAF). (matrix presented)
16. Optimal results were obtained with an excess of sulfonyl halide; use of a single equivalent of sulfonyl halide resulted in a reduced yield. For example, treatment of Wang resin with 1 equiv of p-toluenesulfonyl chloride followed by hydrolysis provided the sulfonic acid in 49% yield.
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19. The immobilization of p-toluenesulfonate on Wang resin and its recovery is illustrative: to the Wang hydroxy functionalized resin (50 mg, 0.8 mmol/g) in dichloromethane were added 10 equiv of diisopropylethylamine (52 mg) and 5 equiv of the arenesulfonyl chloride (38 mg). The mixture was shaken overnight. Solvent was then drained off, and the resin was washed successively with methylene chloride, acetonitrile, methanol, and again with methylene chloride. Cleavage of the product from the resin was accomplished by treatment with trifluoroacetic acid in methylene chloride (5:95) for 1 h. Collection of the solvent followed by evaporation provided the sulfonic acid (8.7 mg, 92%).
20. All sulfonic acids were analyzed by HPLC, NMR, and MS and exhibit spectroscopic and chromatographic data identical to authentic samples.
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25. 3OH. The combined organic elutions were evaporated to give essentially pure 4-methylbiphenylsulfonic acid (5.1 mg, 55%).
26. All products gave satisfactory NMR and mass spectral data and are identical to published data, where available. Biphenyl-4-sulfonic acid and 4′-methylbiphenyl-4-sulfonic acid have been prepared previously: Kortekaas, T. A.; Cerfontain, H. J. Chem. Soc., Perkin Trans. 2 1977, 1560-1562.
27. Casalnuovo, A. L.; Calabrese, J. C. J. Am. Chem. Soc. 1990, 112, 4324-4330.