Synlett

An efficient organocatalyzed interconversion of silyl ethers to tosylates using DBU and p-toluenesulfonyl fluoride

V Gembus, F Marsais, V Levacher

Index: Gembus, Vincent; Marsais, Francis; Levacher, Vincent Synlett, 2008 , # 10 p. 1463 - 1466

Full Text: HTML

Citation Number: 16

Abstract

Abstract A mild and efficient interconversion from silyl ethers to sulfonates esters is reported with good yields. This silyl-sulfonyl exchange proceeds readily in acetonitrile at room temperature in the presence of p-toluenesulfonyl fluoride and a catalytic amount of 1, 8- diazabicyclo [5.4. 0] undec-7ene (DBU). This method can be used with trimethysilyl (TMS), triethylsilyl (TES) and tert-butyldimethylsilyl (TBDMS) ethers.

Related Articles:

Practical and efficient methods for sulfonylation of alcohols using Ts (Ms) Cl/Et 3 N and catalytic Me 3 H· HCl as combined base: Promising alternative to traditional …

[Yoshida, Yoshihiro; Sakakura, Yoshiko; Aso, Naoya; Okada, Shin; Tanabe, Yoo Tetrahedron, 1999 , vol. 55, # 8 p. 2183 - 2192]

Efficient and mild ytterbium (III)-catalyzed tosylation of alcohols

[Comagic, Slobodan; Schirrmacher, Ralf Synthesis, 2004 , # 6 p. 885 - 888]

Nucleophilic substitution of alkyl iodides via oxidative ligand transfer

[Macdonald, Timothy L.; Narasimhan, Narayanan Journal of Organic Chemistry, 1985 , vol. 50, # 24 p. 5000 - 5001]

Novel method of deoxidation of alcohols and its use in synthesis of covalent perchlorates

[Tetrahedron Letters, , vol. 26, # 50 p. 6243 - 6244]

Reaction of phosphorus oxyacid esters with p-toluenesulfonic acid.

[Chemical and Pharmaceutical Bulletin, , vol. 34, # 7 p. 2710 - 2718]

More Articles...