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Photoinduced Atom Transfer Radical Addition/Cyclization Reaction between Alkynes or Alkenes with Unsaturated α-Halogenated Carbonyls. | LitMetric

AI Article Synopsis

  • - The researchers created a photochemical reaction (ATRA/ATRC) that uses halogen bonding to facilitate reactions between bromine or iodine-containing malonic acid esters and alkenes/alkynes under visible light.
  • - Through control experiments, they discovered that halogen-bonding interactions help form complexes of amines and halogens, which activate the cleavage of carbon-halogen bonds when exposed to light, creating carbon radicals.
  • - This innovative method allows for a range of substrate use, yielding products like cyclopentenes and cyclopentanes via intermolecular addition and intramolecular cyclization.

Article Abstract

We have developed a photochemical ATRA/ATRC reaction that is mediated by halogen bonding interactions. This reaction is caused by the reaction of malonic acid ester derivatives containing bromine or iodine with unsaturated compounds such as alkenes and alkynes in the presence of diisopropylethylamine under visible light irradiation. As a result of various control experiments, it was found that the formation of complexes between amines and halogens by halogen-bonding interaction occurs in the reaction system, followed by the cleavage of the carbon-halogen bonds by visible light, resulting in the formation of carbon radicals. In this reaction, a variety of substrates can be used, and the products, cyclopentenes and cyclopentanes, were obtained by intermolecular addition and intramolecular cyclization.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8618827PMC
http://dx.doi.org/10.3390/molecules26226781DOI Listing

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