4.6 Article

An Alternative Method for Generating Arynes from ortho-Silylaryl Triflates: Activation by Cesium Carbonate in the Presence of a Crown Ether

Journal

MOLECULES
Volume 20, Issue 6, Pages 10131-10140

Publisher

MDPI
DOI: 10.3390/molecules200610131

Keywords

aryne; ortho-silylaryl triflate; cesium carbonate; crown ether

Funding

  1. Platform for Drug Discovery, Informatics, and Structural Life Science from MEXT, Japan
  2. JSPS KAKENHI [15H03118, 26350971]
  3. Azuma Medical AMP
  4. Dental Research Grant
  5. Grants-in-Aid for Scientific Research [26350971, 15H03118] Funding Source: KAKEN

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An alternative method for generating arynes from ortho-silylaryl triflates using cesium carbonate and 18-crown-6 is reported. The method was efficiently applied to a variety of reactions between several arynes and arynophiles. We also demonstrated that the efficiency of aryne generation is significantly affected by the alkali metal countercation of the carbonate.

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