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Synlett 2014; 25(10): 1419-1424
DOI: 10.1055/s-0033-1339004
letter
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Diarylation of Activated Alkenes with Diaryliodonium Salts

Yang Yang
a   Key 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*
b   Shanghai-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
a   Key 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
a   Key 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
a   Key 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*
a   Key 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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Further Information

Publication History

Received: 24 February 2014

Accepted after revision: 07 April 2014

Publication Date:
19 May 2014 (online)

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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

Supporting Information

    for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000083.
  • Supporting Information
 

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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.