4.8 Article

Rhodium-Catalyzed Reductive trans-Alkylacylation of Internal Alkynes via a Formal Carborhodation/C-H Carbonylation Cascade

Journal

ORGANIC LETTERS
Volume 23, Issue 13, Pages 5039-5043

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01568

Keywords

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Funding

  1. National Natural Science Foundation of China [21625203, 21871126]
  2. Opening Fund of KLCBTCMR, Ministry of Education [KLCBTCMR1802]
  3. Hunan Provincial Innovation Foundation for Postgraduates [CX20200448]

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This method of rhodium-catalyzed reductive annulation cascade reaction avoids the need for prefunctionalization by using the Mn reductant to reductively regenerate the active rhodium species. It provides a new route for the carbonylation of aromatic C-H bonds with alkynes leading to aryl vinyl ketone frameworks.
A rhodium-catalyzed reductive annulation cascade reaction that consists of a formal anti-carborhodation of a C C bond and an aromatic C-H carbonylation cascade for producing cyclopenta[de]quinoline-2,5(1H,3H)-diones is described. This method uses the Mn reductant to reductively regenerate the active rhodium species, hence obviating the need for prefunctionalization, and represents a new route to the carbonylation of aromatic C-H bonds with alkynes leading to aryl vinyl ketone frameworks.

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