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Synlett 2013; 24(15): 1959-1962
DOI: 10.1055/s-0033-1339448
DOI: 10.1055/s-0033-1339448
letter
Copper-Catalyzed Direct N-Arylation of Naphthalimides Using Diaryliodonium Salts
Weitere Informationen
Publikationsverlauf
Received: 07. Mai 2013
Accepted after revision: 18. Juni 2013
Publikationsdatum:
07. August 2013 (online)
Abstract
An effective copper-catalyzed N-arylation of naphthal-imides with diaryliodonium salts in toluene at 100 °C has been developed. This cross-coupling reaction gives the desired N-arylated 1,8-naphthalimides in moderate to good yields. The synthetic potential of this coupling is applied in functional materials based on N-arylated 1,8-naphthalimides, such as molecular probes.
Key words
arylation - copper catalysis - diaryliodonium salts - naphthalimides - C–N cross couplingSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
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- 21 N-Arylation of Naphthalimides with Diaryliodonium Salts; General Procedure: A mixture of 1,8-naphthalimide (0.4 mmol), diaryliodonium salt (0.48 mmol), t-BuOK (2 equiv), CuI (10 mmol%) and toluene (3 mL) was taken in a 10 mL reaction tube and heated at 100 °C for 0.5–2 h under vigorous stirring. After completion of the reaction, as indicated by TLC, the reaction mixture was concentrated under reduced pressure, and the crude compound was purified by chromatography on a silica gel column (EtOAc–petroleum ether) to afford the desired product.
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