Improved syntheses of halogenated benzene-1,2,3,4-tetracarboxylic diimides

• DOI: 10.26434/chemrxiv-2021-xcbvc
• Publication Date: 2022-02-01T15:04:39Z
• Authors: Brian Zou; Kellie A. Stellmach; Stella M. Luo; Feven L. Gebresil...; Cathy K. Zhang; Adam D. Bass; Daron E. Janzen; Dennis D. Cao
• Keywords: Reactivity; Diimide; Benzene derivatives

The preparation of halogenated benzene-1,2,3,4-tetracarboxylic diimide derivatives is challenging because the possibility competitive incorrect cyclizations and SNAr reactivity. Here, we demonstrate that direct reaction acids with primary amines in acetic acid solvent successfully provides a range desirable ortho-diimide products good yields. Furthermore, sterically N-derivatizations can be readily achieved under microwave reactor conditions, reactivity only observed when excess amine used. diimides described here are attractive building blocks for organic materials chemistry.