4.8 Article

Iron-catalyzed carbonylation of aryl halides with arylborons using stoichiometric chloroform as the carbon monoxide source

Journal

GREEN CHEMISTRY
Volume 18, Issue 21, Pages 5782-5787

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c6gc02158a

Keywords

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Funding

  1. Natural Science Foundation of Jiangsu Province [BK20161553]
  2. Natural Science Foundation of China [21302099]
  3. Natural Science Foundation of Jiangsu Provincial Colleges and Universities [16KJB150019]
  4. SRF for ROCS, SEM
  5. Qing Lan project of Nanjing Normal University
  6. Priority Academic Program Development of Jiangsu Higher Education Institutions

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A general iron-catalyzed carbonylative Suzuki-Miyaura coupling of aryl halides with arylborons is reported, using stoichiometric CHCl3 as the CO source. The high efficiency, economy, selectivity, and operational simplicity of this transformation make this method a valuable tool in organic synthesis. Importantly, the presented strategy allows effective C-13 labeling simply by using the commercially available C-13-labeled CHCl3. On the basis of the initial mechanistic exploration, an aryl radical intermediate is proposed in the present carbonylation process.

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