4.8 Article

Rh(III)-Catalyzed [5+1] Annulation of Indole-enaminones with Diazo Compounds To Form Highly Functionalized Carbazoles

Journal

ORGANIC LETTERS
Volume 23, Issue 11, Pages 4406-4410

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01341

Keywords

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Funding

  1. National Natural Science Foundation of China [21977106, 21632008]
  2. Shanghai Science and Technology Development Funds [19431901000, 19431901200]
  3. Science and Technology Commission of Shanghai Municipality [18JC1411304]
  4. Youth Innovation Promotion Association CAS

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A novel Rh(III)-catalyzed C-H activation/annulation cascade of indole-enaminones with diazo compounds was reported, generating diversely functionalized carbazole frameworks with good to excellent yields. The most notable feature is the formation of a novel [5 + 1] cyclization product, accompanied by the complete removal of acetyl and N,N-dimethyl groups from the substrates, rather than the expected [4 + 2] cyclization products.
A novel Rh(III)-catalyzed C-H activation/annulation cascade of indole-enaminones with diazo compounds was reported to construct diversely functionalized carbazole frameworks. The most notable characteristic is that this transformation could smoothly furnish a novel [5 + 1] cyclization product with good to excellent yields (up to 95%), accompanied by the thorough removal of acetyl and N,N-dimethyl groups of two substrates from the target products, rather than the normally expected [4 + 2] cyclization products.

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