4.8 Article

Palladium-Catalyzed Cycloisomerization of 2-Ethynylbiaryls to9-Methylidene Fluorenes

Journal

ORGANIC LETTERS
Volume 24, Issue 14, Pages 2596-2600

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c00534

Keywords

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Funding

  1. National Natural Science Foundation of China [21573032, 21602026]
  2. Fundamental Research Funds for the Central Universities [DUT20LK42]
  3. LiaoNing Revitalization Talents Program [XLYC1802030]
  4. Natural Science Foundation of Liaoning, China [2019JH3/30100001]

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A palladium-catalyzed cycloisomerization of 2-ethynylbiaryls to 9-methylidenefluorenes is described for the first time. This method is operationally simple and scalable, and exhibits high functional group tolerance.
A palladium-catalyzed cycloisomerization of 2-ethynylbiaryls to 9-methylidenefluorenes is described for thefirst time.The cycloisomerization of 2-ethynylbiaryls proceeded smoothly in the presence of weak acid at low temperature to afford 9-methylidenefluorenes in satisfactory to high yields. This new type of cycloisomerization of 2-ethynylbiaryls is operationally simpleand scalable and exhibits high functional-group tolerance. Various synthetically useful functional groups, such as halogen atoms, aswell as formyl, acetyl, methoxycarbonyl, cyano, and nitro groups, remain intact during the cycloisomerization of 2-ethynylbiaryls.

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