4.8 Article

Hexafluoroisopropanol-Promoted or Bronsted Acid-Mediated Photochemical [2+2] Cycloadditions of Alkynes with Maleimides

期刊

CHEMSUSCHEM
卷 15, 期 4, 页码 -

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/cssc.202102441

关键词

[2+2]-cycloadditions; alkynes; maleimides; organocatalysis; photochemistry

资金

  1. Hellenic Foundation for Research and Innovation (HFRI) [721, 655]
  2. State Scholarships Foundation (IKY) [MIS 5033021]
  3. European Social Fund (ESF)
  4. State Scholarships Foundation (IKY)
  5. European Union (European Social Fund-ESF) through the Operational Programme Human Resources Development, Education and Lifelong Learning [MIS-5000432]

向作者/读者索取更多资源

This paper investigates the photocatalytic reaction between alkynes and maleimides, comparing the reactivity differences between N-alkyl and N-aryl maleimides. The results show that using hexafluoroisopropanol or trifluoroacetic acid as solvents can achieve high yields in the reaction.
Although the use of light stimulating organic transformations has been known for more than a century, there is an increasing research interest on expanding the established knowledge. While [2+2] cycloadditions are promoted photochemically, literature precedent on the reaction between alkynes and maleimides is limited and only a handful of examples exist, focusing mainly on N-aliphatic maleimides. Herein, the differences in reactivity between N-alkyl and N-aryl maleimides were identified, and the use of hexafluoroisopropanol (HFIP) or trifluoroacetic acid (TFA) as viable solutions was proposed in order to achieve high yields. In the case of N-alkyl maleimides, both HFIP-mediated or TFA-promoted reactions were established using LED 370 nm irradiation, without the use of an external photocatalyst. In the case of N-aryl maleimides, thioxanthone (THX) was employed as the energy transfer photocatalyst along with LED 427 nm irradiation and HFIP. Mechanistic studies were performed, supporting the pivotal role of HFIP or TFA, in acquiring good to high yields in both classes of maleimides.

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