Bronsted acid-catalyzed 1,4-addition of 1,3,5-trimethoxybenzene to maleimides and acrylates

Several Bronsted acids were investigated as catalysts for 1,4-additions of 1,3,5-trimethoxybenzene to maleimides. Among the acids tested, trifluoromethanesulfonic acid in low polar solvents such as toluene and 1,2-dichloroethane was found to show high reactivity, enabling preparation of 3-2,4,6-trimethoxyphenyl)succinimides. 1,4-Additions of 1,3,5-trimethoxybenzene to acrylates were also realized by a catalytic amount of trifluoromethanesulfonic acid in toluene. (C) 2021 Elsevier Ltd. All rights reserved.

Automated summary

Through investigating Bronsted acids as catalysts, trifluoromethanesulfonic acid was found to exhibit high catalytic activity in low-polar solvents for the 1,4-addition reactions, enabling the synthesis of succinimides. Furthermore, a catalytic amount of trifluoromethanesulfonic acid in toluene could also realize the 1,4-addition reactions of 1,3,5-trimethoxybenzene to acrylates.