Sulfonyl Chloride Resin

Sulfonyl chloride resin is a widely used reagent and can be applied in organic synthesis. It can react with alcohols to generate polymer-supported tosylates, which can then be cleaved with nucleophiles to generate secondary and tertiary amine, thioethers and N-alkylimidazoles [1-3]. This approach has been employed to prepared oxazolidinones by a cyclative cleavage strategy involving intramolecular aminolysis of the polymer-bound tosylate [4]. It can also be used as an efficient solid-supported condensation reagent for the solution phase synthesis of esters [5] or a derivative azide transfer reagent to prepare α-diazo ketones [6]. Chiral amine can also be supported on this resin to reduce the aromatic ketone to secondary alcohols [7].

References

[1] J. J. Reuter, et al., Tetrahedron Lett., 1998, 39, 975
[2] E. W. Baxter, et al., Tetrahedron Lett., 1998, 39, 979
[3] Y. Hu, et al., ECSOC-2 www.mdpi.org/ecsoc, b0003, 1998
[4] P. T. Holte, et al., Eur. J. Org. Chem., 2001, 2965
[5] N. Zander, et al., Tetrahedron Lett., 2001, 42, 7783
[6] M. Gary, et al., J. Org., Chem., 2001, 66, 2509
[7] J. B. Hu, et al., J. Org. Chem., 2001, 66, 303