Copper-promoted N-arylations of cyclic imides within six-membered rings

A facile route to arylene-based organic materials

Erin T. Chernick, Michael J. Ahrens, Karl A. Scheidt, Michael R Wasielewski

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

(Chemical Equation Presented) 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.

Original languageEnglish
Pages (from-to)1486-1489
Number of pages4
JournalJournal of Organic Chemistry
Volume70
Issue number4
DOIs
Publication statusPublished - Feb 18 2005

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Imides
Copper
Aniline Compounds
Perylene
Heating
Anhydrides
Amines
Esters
Coloring Agents
Oxygen

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Copper-promoted N-arylations of cyclic imides within six-membered rings : A facile route to arylene-based organic materials. / Chernick, Erin T.; Ahrens, Michael J.; Scheidt, Karl A.; Wasielewski, Michael R.

In: Journal of Organic Chemistry, Vol. 70, No. 4, 18.02.2005, p. 1486-1489.

Research output: Contribution to journalArticle

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