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

Vinod H. Jadhav; Sang Bong Lee; Hwan Jeong Jeong; Seok Tae Lim; Myung Hee Sohn; Dong Wook Kim

doi:10.1016/j.tetlet.2012.02.016

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

Vinod H. Jadhav
, Sang Bong Lee
, Hwan Jeong Jeong
, Seok Tae Lim
, Myung Hee Sohn
, Dong Wook Kim^*

^*Corresponding author for this work

Department of Medicine

Jeonbuk National University

Research output: Contribution to journal › Journal article › peer-review

16 Scopus citations

Abstract

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 CH ₃CN solvent instead of tert-alcohol at 100 °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.

Original language	English
Pages (from-to)	2051-2053
Number of pages	3
Journal	Tetrahedron Letters
Volume	53
Issue number	16
DOIs	https://doi.org/10.1016/j.tetlet.2012.02.016
State	Published - 2012.04.18

Keywords

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

Quacquarelli Symonds(QS) Subject Topics

Engineering - Petroleum
Pharmacy & Pharmacology
Chemistry
Biological Sciences

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10.1016/j.tetlet.2012.02.016

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@article{262cc07d889e417d851493492852f6ae,

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

abstract = "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 CH 3CN solvent instead of tert-alcohol at 100 °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.",

keywords = "Chemoselective deprotection, Desilylation, Fluoride, Ionic liquid, tert-Alcohol, tert-Butyldimethylsilyl group",

author = "Jadhav, \{Vinod H.\} and Lee, \{Sang Bong\} and Jeong, \{Hwan Jeong\} and Lim, \{Seok Tae\} and Sohn, \{Myung Hee\} and Kim, \{Dong Wook\}",

year = "2012",

month = apr,

day = "18",

doi = "10.1016/j.tetlet.2012.02.016",

language = "English",

volume = "53",

pages = "2051--2053",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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TY - JOUR

T1 - An efficient and chemoselective deprotection of tert-butyldimethylsilyl (TBDMS) ethers using tailor-made ionic liquid

AU - Jadhav, Vinod H.

AU - Lee, Sang Bong

AU - Jeong, Hwan Jeong

AU - Lim, Seok Tae

AU - Sohn, Myung Hee

AU - Kim, Dong Wook

PY - 2012/4/18

Y1 - 2012/4/18

N2 - 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 CH 3CN solvent instead of tert-alcohol at 100 °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.

AB - 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 CH 3CN solvent instead of tert-alcohol at 100 °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.

KW - Chemoselective deprotection

KW - Desilylation

KW - Fluoride

KW - Ionic liquid

KW - tert-Alcohol

KW - tert-Butyldimethylsilyl group

UR - https://www.scopus.com/pages/publications/84862812356

U2 - 10.1016/j.tetlet.2012.02.016

DO - 10.1016/j.tetlet.2012.02.016

M3 - Journal article

AN - SCOPUS:84862812356

SN - 0040-4039

VL - 53

SP - 2051

EP - 2053

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 16

ER -

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

Abstract

Keywords

Quacquarelli Symonds(QS) Subject Topics

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