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

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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.