Synlett 2013; 24(15): 1959-1962
DOI: 10.1055/s-0033-1339448
letter
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Direct N-Arylation of Naphthalimides Using Diaryliodonium Salts

Song Mao
a  Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China   Fax: +86(21)64253881   Email: [email protected]
,
Fenglou Guo
a  Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China   Fax: +86(21)64253881   Email: [email protected]
,
Juan Li
a  Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China   Fax: +86(21)64253881   Email: [email protected]
,
Xu Geng
a  Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China   Fax: +86(21)64253881   Email: [email protected]
,
Jianjun Yu
a  Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China   Fax: +86(21)64253881   Email: [email protected]
,
Jianwei Han
c  Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. of China
,
Limin Wang*
a  Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China   Fax: +86(21)64253881   Email: [email protected]
b  Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences, 345 Ling Ling Road, Shanghai 200237, P. R. of China
› Author Affiliations
Further Information

Publication History

Received: 07 May 2013

Accepted after revision: 18 June 2013

Publication Date:
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.

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.