Cargando…
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...
Autores principales: | , , , |
---|---|
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 |
_version_ | 1783628594944147456 |
---|---|
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. |
format | Online Article Text |
id | pubmed-7765919 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT chinahideyasu halogeninducedcontrollablecyclizationsasdiverseheterocyclesyntheticstrategy AT kumarravi halogeninducedcontrollablecyclizationsasdiverseheterocyclesyntheticstrategy AT kikushimakotaro halogeninducedcontrollablecyclizationsasdiverseheterocyclesyntheticstrategy AT dohitoshifumi halogeninducedcontrollablecyclizationsasdiverseheterocyclesyntheticstrategy |