An efficient and chemoselective deprotection of tert-butyldimethylsilyl (TBDMS) ethers using tailor-made ionic liquid

作者：Jadhav Vinod H; Lee Sang Bong; Jeong Hwan Jeong; Lim Seok Tae; Sohn Myung Hee; Kim Dong Wook^*

来源：Tetrahedron Letters, 2012, 53(16): 2051-2053.

DOI：10.1016/j.tetlet.2012.02.016

• Chemoselective deprotection
• Desilylation
• tert-Butyldimethylsilyl group
• Ionic liquid
• tert-Alcohol
• Fluoride

Phenolic tert-butyldimethylsilyl (TBDMS) ethers can be deprotected to yield phenols in excellent yield using tailor-made ionic liquid [dihexaEGim][OMs] (dihexaEGim = dihexaethylene glycolic imidazolium salt) as an organic catalyst with alkali-metal fluoride in tert-amyl alcohol. On the contrary, all TBDMS protecting groups can be cleaved cleanly from the bis-TBDMS ether using the same reaction in CH3CN solvent instead of tert-alcohol at 100 degrees C. This [dihexaEGim][OMs]/tert-amyl alcohol media system allows the highly selective phenolic deprotection reaction of various bis-TBDMS ethers containing both phenolic and aliphatic TBDMS ethers to provide the corresponding phenols in high yield.

• 出版日期2012-4-18