4.5 Article

Gold and TfOH-Cocatalyzed Tandem Reaction of ortho-Akynylarylaldehydes with Cyclopropenes: an Efficient Route to Functionalized Benzo[7]annulene Derivatives

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2019, Issue 9, Pages 1952-1956

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201900118

Keywords

Cycloheptene; Gold catalysis; Cyclopropene; Ring expansion; Alkynylbenzaldehyde

Funding

  1. NSFC [21402106]
  2. SRF for ROCS, SEM [20141685]
  3. Shandong Natural Science Foundation [ZR2018JL013, ZR2018MB014, ZR2014BQ024]
  4. Higher Educational Science and Technology Program [J15LA02]
  5. Qufu Normal University for Research Start-up Foundation

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A novel gold(III) and TfOH-cocatalyzed reaction of ortho-alkynylbenzaldehydes with cyclopropenes was described for the synthesis of a variety of functionalized benzo[7]annulene derivatives in a highly stereoselective manner. This reaction could undergo tandem [4+2] cycloaddition/ring expansion to achieve the construction of seven-membered-carbocycles, along with the cleavage of double bond of cyclopropenes. The reaction features simple operations, commercially available catalysts and broad substrate scope with good efficiencies.

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