4.7 Article

Palladium-Catalyzed Heck-type Domino Cyclization and Carboxylation to Synthesize Carboxylic Acids by Utilizing Chloroform as the Carbon Monoxide Source

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 15, Pages 7547-7554

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b01126

Keywords

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Funding

  1. 973 project from the MOST of China [2015CB856600]
  2. NSFC [21272221, 21472179]
  3. Recruitment Program of Global Experts
  4. Fundamental Research Funds for the Central Universities [WK 2060190028, 2060190026, 3430000001]
  5. Fundamental Research Funds for Central Universities
  6. Cross-disciplinary Collaborative Teams Program for Science, Technology and Innovation from Chinese Academy of Sciences

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A palladium-catalyzed domino cyclization and carboxylation reaction for synthesis of a variety of carboxylic acids was developed, where chloroform was used as carbon monoxide source. The in situ generated neopentylpalladium species by Heck cyclization was efficiently trapped by dichlorocarbene to form a series of carboxylic acids. It was found that in this type of domino reaction CHCl3 is a convenient and safe alternation for CO gas.

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