4.8 Article

Palladium(II) Acetate Catalyzed Tandem Cycloisomerization and Oxidation of Arylvinylcyclopropenes Using p-Benzoquinone as Oxidant and Pro-nucleophile

Journal

ORGANIC LETTERS
Volume 11, Issue 22, Pages 5278-5281

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol902233r

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Funding

  1. Shanghai Municipal Committee of Science and Technology [06XD14005, 08dj1400100-2]
  2. National Basic Research Program of China [2009CB825300]
  3. National Natural Science Foundation of China [20872162, 20672127, 20732008, 20821002, 20702013]

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Catalyzed by Pd(II)/p-BQ, a tandem cycloisomerization and oxidation of arylvinylcyclopropenes took place smoothly to produce methyleneindene derivatives stereoselectively in moderate to excellent yields, affording an unusual example of solo addition by p-hydroquinone generated by oxidation of Pd(0) to Pd(II) along with the formation of a new C-O bond.

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