4.8 Article

Rh(III)-Catalyzed Coupling of Acrylic Acids and Ynenones via Olefinic C-H Activation and Michael Addition

Journal

ORGANIC LETTERS
Volume 22, Issue 2, Pages 438-442

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b04191

Keywords

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Funding

  1. NSFC [21525208, 21801066]
  2. Henan Educational Committee [19A150028, 20B350001]
  3. Henan Normal University [qd16111, 2019QK04]
  4. Natural Science Foundation of Henan Province [182300410131]

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Rh(III)-catalyzed coupling between acrylic acids and yndienones has been realized for the synthesis of cis-hydrobenzofuranone. The reaction proceeded in excellent regio- and stereoselectivity under mild and redox-neutral conditions via a sequence of carboxylic acid-directed olefinic C-H activation, alkyne insertion, and Michael addition. Representative products were found to exhibit cytotoxicity toward the A549 cancer cell line at micromolar levels.

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