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Volume 26
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10.3390/molecules26226781
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Communication

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

by
Kazuki Matsuo
,
Tadashi Yoshitake
,
Eiji Yamaguchi
* and
Akichika Itoh
*
Department of Pharmacy, Gifu Pharmaceutical University, 1-25-4 Daigaku-Nishi, Gifu 501-1196, Japan
*
Authors to whom correspondence should be addressed.
Molecules 2021, 26(22), 6781; https://doi.org/10.3390/molecules26226781
Submission received: 28 September 2021 / Revised: 3 November 2021 / Accepted: 7 November 2021 / Published: 10 November 2021
(This article belongs to the Special Issue Green and Highly Efficient One-Pot Synthesis and Catalysis)
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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.
Keywords: halogen-bonding; ATRA reaction; ATRC reaction; radical reaction; photoreaction halogen-bonding; ATRA reaction; ATRC reaction; radical reaction; photoreaction
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MDPI and ACS Style

Matsuo, K.; Yoshitake, T.; Yamaguchi, E.; Itoh, A. Photoinduced Atom Transfer Radical Addition/Cyclization Reaction between Alkynes or Alkenes with Unsaturated α-Halogenated Carbonyls. Molecules 2021, 26, 6781. https://doi.org/10.3390/molecules26226781

AMA Style

Matsuo K, Yoshitake T, Yamaguchi E, Itoh A. Photoinduced Atom Transfer Radical Addition/Cyclization Reaction between Alkynes or Alkenes with Unsaturated α-Halogenated Carbonyls. Molecules. 2021; 26(22):6781. https://doi.org/10.3390/molecules26226781

Chicago/Turabian Style

Matsuo, Kazuki, Tadashi Yoshitake, Eiji Yamaguchi, and Akichika Itoh. 2021. "Photoinduced Atom Transfer Radical Addition/Cyclization Reaction between Alkynes or Alkenes with Unsaturated α-Halogenated Carbonyls" Molecules 26, no. 22: 6781. https://doi.org/10.3390/molecules26226781

APA Style

Matsuo, K., Yoshitake, T., Yamaguchi, E., & Itoh, A. (2021). Photoinduced Atom Transfer Radical Addition/Cyclization Reaction between Alkynes or Alkenes with Unsaturated α-Halogenated Carbonyls. Molecules, 26(22), 6781. https://doi.org/10.3390/molecules26226781

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