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

Song Mao; Fenglou Guo; Juan Li; Xu Geng; Jianjun Yu; Jianwei Han; Limin Wang

doi:10.1055/s-0033-1339448

Synlett, Table of Contents

Synlett 2013; 24(15): 1959-1962
DOI: 10.1055/s-0033-1339448

letter

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

Song Mao

^aKey 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: wanglimin@ecust.edu.cn

,

Fenglou Guo

^aKey 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: wanglimin@ecust.edu.cn

,

Juan Li

^aKey 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: wanglimin@ecust.edu.cn

,

Xu Geng

^aKey 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: wanglimin@ecust.edu.cn

,

Jianjun Yu

^aKey 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: wanglimin@ecust.edu.cn

,

Jianwei Han

^cKey Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. of China

,

Limin Wang*

^aKey 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: wanglimin@ecust.edu.cn

^bShanghai-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

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Abstract

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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 coupling

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References

References and Notes

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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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