4.8 Article

Palladium-Catalyzed Sequential Carbon-Carbon Bond Cleavage/Formation Producing Arylated Benzolactones

Journal

ORGANIC LETTERS
Volume 10, Issue 22, Pages 5219-5221

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol802218a

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Funding

  1. Asahi Glass Foundation
  2. Ministry of Education, Culture, Sports, Science and Technology, Japan [19205013]
  3. Japan Society for the Promotion of Science
  4. Grants-in-Aid for Scientific Research [19205013] Funding Source: KAKEN

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3-(2-Hydroxyphenyl)cyclobutanones react with aryl bromides in the presence of palladium catalysts to afford 4-arylmethyl-3,4-dihydrocoumarins in high yields through a sequence involving carbon-carbon bond cleavage and formation. In the case of the reaction with 2-(2-hydroxyphenyl)cyclobutanones, five- or seven-membered lactones were produced depending on the presence of an additional substituent at the 2-position.

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