One-Pot Approach to Installing Eight-Membered Rings onto Indoles

Authors

  • Can Zhu,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (P.R. China)
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  • Xue Zhang,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (P.R. China)
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  • Xiongdong Lian,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (P.R. China)
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  • Prof. Dr. Shengming Ma

    Corresponding author
    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (P.R. China)
    2. Shanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry, East China Normal University, 3663 North Zhongshan Lu, Shanghai 200062 (P.R. China)
    • State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (P.R. China)
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  • Financial support from the Major State Basic Research and Development Program (2011CB808700) and the NSF of China (21102164 for the DFT calculation) is acknowledged. We thank G. Chai of our research group for reproducing the results presented in entries 3 and 14 of Table 2.

Abstract

original image

Achtring angesetzt: Pd0-katalysierte Reaktionen von 2-Allyl-3-iod-1-tosyl-1H-indolen mit Propargylbromiden ergeben Dihydrocycloocta[b]indole (siehe Schema) über eine C-C-Kupplung, eine [1,5]-Wasserstoffverschiebung und eine Elektrocyclisierung. Die Methode eröffnet einen effizienten Zugang zu Iprindol.

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