Copper-Catalyzed Diarylation of Activated Alkenes with Diaryliodonium Salts

Yang Yang; Jianwei Han; Xunshen Wu; Song Mao; Jianjun Yu; Limin Wang

doi:10.1055/s-0033-1339004

Synlett, Table of Contents

Synlett 2014; 25(10): 1419-1424
DOI: 10.1055/s-0033-1339004

letter

Copper-Catalyzed Diarylation of Activated Alkenes with Diaryliodonium Salts

Yang Yang

^aKey Laboratory of 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*

^bShanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences, 345 Ling Ling Road, Shanghai, 200032, P. R. of China Fax: +86(21)54925583 Email: jianweihan@sioc.ac.cn

,

Xunshen Wu

^aKey Laboratory of 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

,

Song Mao

^aKey Laboratory of 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 of 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

,

Limin Wang*

^aKey Laboratory of 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

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Abstract

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Abstract

Cu(OTf)₂-catalyzed diarylation of activated alkenes by using diaryliodonium(III) salts has been developed. With this method, arylated oxindoles can be easily accessed in good yields. Insights into the mechanism of copper-catalyzed arylations are discussed, and the findings are expected to help increase the level of understanding of catalytic arylations with diaryliodonium salts.

Key words

alkene activation - arylation - diaryliodonium salts - oxindoles - copper triflate

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References

References and Notes

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14 Cascade Reaction of N-Arylacrylamide with Diaryliodonium Salts; General Procedure: Cu(OTf)₂ (0.05 mmol, 0.1 equiv), N-arylacrylamide (0.5 mmol, 1.0 equiv) and diphenyliodonium salt (1.0 mmol, 2.0 equiv) were added to a dried Schlenk tube. The tube was degassed with nitrogen three times, then DCE (2.0 mL) was added by using a syringe. The mixture was heated and stirred at 130 °C for 16 h, then cooled to r.t. and the solvent was evaporated in vacuum. The crude products were directly purified by flash column chromatography on silica gel (petroleum ether–EtOAc, 10:1) to afford the desired oxindole.

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