4.8 Article

Expedient Synthesis of Phenanthrenes via In(III)-Catalyzed 6-Exo-Dig Cycloisomerization

Journal

ORGANIC LETTERS
Volume 15, Issue 4, Pages 920-923

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol400073s

Keywords

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Funding

  1. Midcareer Researcher Program [KRF-2010-0027312]
  2. World Class University Program of the National Research Foundation of Korea (NRF) grant [R32-2008-000-10098-0]
  3. Korean Government (MEST)
  4. NRF (NRF-2012-Fostering Core Leaders of the Future Basic Science Program)
  5. National Research Foundation of Korea [R32-2008-000-10098-0, 2010-0027312] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)

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This paper documents the first example of In(III)-catalyzed selective 6-exo-dig hydroarylation of o-propargylblaryls and their subsequent double-bond migration to obtain functionalized phenanthrenes. Electron-rich biaryl substrates undergo hydroarylation more effectively, and the substrates with various types of substituents on the alkyne can also be smoothly and selectively converted to phenanthrenes.

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