Copper-promoted N-arylations of cyclic imides within six-membered rings: a facile route to arylene-based organic materials.
[reaction: see text] Cyclic imides within six-membered rings are shown to undergo efficient N-arylation using various arylboronic esters mediated by copper(II) acetate in the presence of an amine base and oxygen atmosphere with gentle heating. Until now, the synthesis of N-arylated cyclic imides having six-membered rings was restricted largely to strongly heating anilines in the presence of anhydrides. This reaction is applicable to the synthesis of new organic materials based on arylene imide and bis(imide) dyes, such as perylene-3,4:9,10-bis(dicarboximide)s.
Chernick
Erin T
ET
Department of Chemistry and Center for Nanofabrication and Molecular Self-Assembly, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208-3113, USA.
Ahrens
Michael J
MJ
Scheidt
Karl A
KA
Wasielewski
Michael R
MR