Microwave-accelerated Deprotection of Aryl Silyl Ethers
Date of Award
R. David Crouch
The use of microwave irradiation to accelerate a previously reported deprotection of aryl silyl ethers using catalytic lithium acetate (LiOAc) was investigated. t-Butylphenol protected with a t-butyldimethylsilyl (TBS) group was used to identify the optimal reaction conditions for the conversion of aryl silyl ethers into phenols. Then, removal of other common silyl protecting groups such as t-butyldimethylsilyl (TBDPS), triethylsilyl (TES), and triisopropylsilyl (TIPS) from protected phenols was studied under these conditions. Additionally, the ability to perform selective deprotection reactions in which a silyl protecting group is removed from an aryl silyl ether without affecting an alkyl silyl ether in the same molecule was explored. Finally, the sensitivity of normally base sensitive functional groups, such as esters, to the microwave reaction conditions was investigated. By using the microwave to accelerate this reaction, high yields were obtained, while reaction time was decreased when compared to conventional heating, leading to a more efficient method of performing these reactions.
Boyington, Allyson Jane, "Microwave-accelerated Deprotection of Aryl Silyl Ethers" (2015). Dickinson College Honors Theses. Paper 215.