A Simple and Powerful tert-Butylation of Carboxylic Acids and Alcohols

Abstract

A simple and safe tert-butylation reaction was developed. Treatment of various free amino acids with 1.1 equivalents of bis(trifluoromethanesulfonyl)imide in tert-butyl acetate directly afforded tert-butyl esters with free amino groups quickly and in good yields. In addition, various carboxylic acids and alcohols without amino groups were converted into tert-butyl esters and ethers, respectively, in high yields in the presence of small catalytic amounts of bis(trifluoromethanesulfonyl)imide. All tert-butylation reactions of free amino acids, carboxylic acids, and alcohols proceeded much faster and in higher yields compared with conventional methods.

Key words

tert-butylation - amino acids - tert-butyl esters - tert-butyl ethers - bis(trifluoromethanesulfonyl)imide

Publication History

Received: 08 August 2023

Accepted after revision: 29 August 2023

Accepted Manuscript online:
29 August 2023

Article published online:
09 October 2023

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