4.7 Article

BCl3-Activated Synthesis of COO-BODIPY Laser Dyes: General Scope and High Yields under Mild Conditions

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 7, Pages 4594-4601

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b03059

Keywords

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Funding

  1. Ministerio de Ciencia, Innovacion y Universidades de Espana [MAT2017-83856-C3-1-P, MAT2017-83856-C3-2-P, MAT2017-83856-C3-3-P]
  2. Gobierno Vasco [IT912-16]
  3. NIH, Minority Biomedical Research Support [1 SC3 GM089589-08]
  4. Henry Dreyfus Teacher-Scholar Award

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A general and straightforward method for the synthesis of COO-BODIPYs from F-BODIPYs and carboxylic acids is established. The method is based on the use of boron trichloride to activate the involved substitution of fluorine, which leads to high yields through rapid reactions under soft conditions. This mild method opens the way to unprecedented laser dyes with outstanding efficiencies and photostabilities, which are difficult to obtain by the current methods.

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