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Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy

In organic synthesis, due to their high electrophilicity and leaving group properties, halogens play pivotal roles in the activation and structural derivations of organic compounds. Recently, cyclizations induced by halogen groups that allow the production of diverse targets and the structural reorg...

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Autores principales: China, Hideyasu, Kumar, Ravi, Kikushima, Kotaro, Dohi, Toshifumi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7765919/
https://www.ncbi.nlm.nih.gov/pubmed/33353126
http://dx.doi.org/10.3390/molecules25246007
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author China, Hideyasu
Kumar, Ravi
Kikushima, Kotaro
Dohi, Toshifumi
author_facet China, Hideyasu
Kumar, Ravi
Kikushima, Kotaro
Dohi, Toshifumi
author_sort China, Hideyasu
collection PubMed
description In organic synthesis, due to their high electrophilicity and leaving group properties, halogens play pivotal roles in the activation and structural derivations of organic compounds. Recently, cyclizations induced by halogen groups that allow the production of diverse targets and the structural reorganization of organic molecules have attracted significant attention from synthetic chemists. Electrophilic halogen atoms activate unsaturated and saturated hydrocarbon moieties by generating halonium intermediates, followed by the attack of carbon-containing, nitrogen-containing, oxygen-containing, and sulfur-containing nucleophiles to give highly functionalized carbocycles and heterocycles. New transformations of halogenated organic molecules that can control the formation and stereoselectivity of the products, according to the difference in the size and number of halogen atoms, have recently been discovered. These unique cyclizations may possibly be used as efficient synthetic strategies with future advances. In this review, innovative reactions controlled by halogen groups are discussed as a new concept in the field of organic synthesis.
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spelling pubmed-77659192020-12-28 Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy China, Hideyasu Kumar, Ravi Kikushima, Kotaro Dohi, Toshifumi Molecules Review In organic synthesis, due to their high electrophilicity and leaving group properties, halogens play pivotal roles in the activation and structural derivations of organic compounds. Recently, cyclizations induced by halogen groups that allow the production of diverse targets and the structural reorganization of organic molecules have attracted significant attention from synthetic chemists. Electrophilic halogen atoms activate unsaturated and saturated hydrocarbon moieties by generating halonium intermediates, followed by the attack of carbon-containing, nitrogen-containing, oxygen-containing, and sulfur-containing nucleophiles to give highly functionalized carbocycles and heterocycles. New transformations of halogenated organic molecules that can control the formation and stereoselectivity of the products, according to the difference in the size and number of halogen atoms, have recently been discovered. These unique cyclizations may possibly be used as efficient synthetic strategies with future advances. In this review, innovative reactions controlled by halogen groups are discussed as a new concept in the field of organic synthesis. MDPI 2020-12-18 /pmc/articles/PMC7765919/ /pubmed/33353126 http://dx.doi.org/10.3390/molecules25246007 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Review
China, Hideyasu
Kumar, Ravi
Kikushima, Kotaro
Dohi, Toshifumi
Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy
title Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy
title_full Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy
title_fullStr Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy
title_full_unstemmed Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy
title_short Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy
title_sort halogen-induced controllable cyclizations as diverse heterocycle synthetic strategy
topic Review
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7765919/
https://www.ncbi.nlm.nih.gov/pubmed/33353126
http://dx.doi.org/10.3390/molecules25246007
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AT dohitoshifumi halogeninducedcontrollablecyclizationsasdiverseheterocyclesyntheticstrategy