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

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 diisopropylethylamin...

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Autores principales:	Kazuki Matsuo, Tadashi Yoshitake, Eiji Yamaguchi, Akichika Itoh
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	halogen-bonding ATRA reaction ATRC reaction radical reaction photoreaction Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/8788d52a7225445f98ce2cb66b033c1e
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spelling	oai:doaj.org-article:8788d52a7225445f98ce2cb66b033c1e2021-11-25T18:27:13ZPhotoinduced Atom Transfer Radical Addition/Cyclization Reaction between Alkynes or Alkenes with Unsaturated α-Halogenated Carbonyls10.3390/molecules262267811420-3049https://doaj.org/article/8788d52a7225445f98ce2cb66b033c1e2021-11-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/22/6781https://doaj.org/toc/1420-3049We 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.Kazuki MatsuoTadashi YoshitakeEiji YamaguchiAkichika ItohMDPI AGarticlehalogen-bondingATRA reactionATRC reactionradical reactionphotoreactionOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6781, p 6781 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	halogen-bonding ATRA reaction ATRC reaction radical reaction photoreaction Organic chemistry QD241-441
spellingShingle	halogen-bonding ATRA reaction ATRC reaction radical reaction photoreaction Organic chemistry QD241-441 Kazuki Matsuo Tadashi Yoshitake Eiji Yamaguchi Akichika Itoh Photoinduced Atom Transfer Radical Addition/Cyclization Reaction between Alkynes or Alkenes with Unsaturated α-Halogenated Carbonyls
description	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.
format	article
author	Kazuki Matsuo Tadashi Yoshitake Eiji Yamaguchi Akichika Itoh
author_facet	Kazuki Matsuo Tadashi Yoshitake Eiji Yamaguchi Akichika Itoh
author_sort	Kazuki Matsuo
title	Photoinduced Atom Transfer Radical Addition/Cyclization Reaction between Alkynes or Alkenes with Unsaturated α-Halogenated Carbonyls
title_short	Photoinduced Atom Transfer Radical Addition/Cyclization Reaction between Alkynes or Alkenes with Unsaturated α-Halogenated Carbonyls
title_full	Photoinduced Atom Transfer Radical Addition/Cyclization Reaction between Alkynes or Alkenes with Unsaturated α-Halogenated Carbonyls
title_fullStr	Photoinduced Atom Transfer Radical Addition/Cyclization Reaction between Alkynes or Alkenes with Unsaturated α-Halogenated Carbonyls
title_full_unstemmed	Photoinduced Atom Transfer Radical Addition/Cyclization Reaction between Alkynes or Alkenes with Unsaturated α-Halogenated Carbonyls
title_sort	photoinduced atom transfer radical addition/cyclization reaction between alkynes or alkenes with unsaturated α-halogenated carbonyls
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/8788d52a7225445f98ce2cb66b033c1e
work_keys_str_mv	AT kazukimatsuo photoinducedatomtransferradicaladditioncyclizationreactionbetweenalkynesoralkeneswithunsaturatedahalogenatedcarbonyls AT tadashiyoshitake photoinducedatomtransferradicaladditioncyclizationreactionbetweenalkynesoralkeneswithunsaturatedahalogenatedcarbonyls AT eijiyamaguchi photoinducedatomtransferradicaladditioncyclizationreactionbetweenalkynesoralkeneswithunsaturatedahalogenatedcarbonyls AT akichikaitoh photoinducedatomtransferradicaladditioncyclizationreactionbetweenalkynesoralkeneswithunsaturatedahalogenatedcarbonyls
_version_	1718411142068436992

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

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