Three-component coupling of aryl iodides, allenes, and aldehydes catalyzed by a Co/Cr-hybrid catalyst

The cobalt/chromium-catalyzed three-component coupling of aryl iodides, allenes, and aldehydes has been developed to afford multi-substituted homoallylic alcohols in a diastereoselective manner. Control experiments for understanding the reaction mechanism reveal that the cobalt catalyst is involved...

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Autores principales: Komeyama, Kimihiro, Sakiyama, Shunsuke, Iwashita, Kento, Osaka, Itaru, Takaki, Ken
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2018
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6009127/
https://www.ncbi.nlm.nih.gov/pubmed/29977404
http://dx.doi.org/10.3762/bjoc.14.118
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author Komeyama, Kimihiro
Sakiyama, Shunsuke
Iwashita, Kento
Osaka, Itaru
Takaki, Ken
author_facet Komeyama, Kimihiro
Sakiyama, Shunsuke
Iwashita, Kento
Osaka, Itaru
Takaki, Ken
author_sort Komeyama, Kimihiro
collection PubMed
description The cobalt/chromium-catalyzed three-component coupling of aryl iodides, allenes, and aldehydes has been developed to afford multi-substituted homoallylic alcohols in a diastereoselective manner. Control experiments for understanding the reaction mechanism reveal that the cobalt catalyst is involved in the oxidative addition and carbometalation steps in the reaction, whereas the chromium salt generates highly nucleophilic allylchromium intermediates from allylcobalt species, without the loss of stereochemical information, to allow the addition to aldehydes.
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spelling pubmed-60091272018-07-05 Three-component coupling of aryl iodides, allenes, and aldehydes catalyzed by a Co/Cr-hybrid catalyst Komeyama, Kimihiro Sakiyama, Shunsuke Iwashita, Kento Osaka, Itaru Takaki, Ken Beilstein J Org Chem Full Research Paper The cobalt/chromium-catalyzed three-component coupling of aryl iodides, allenes, and aldehydes has been developed to afford multi-substituted homoallylic alcohols in a diastereoselective manner. Control experiments for understanding the reaction mechanism reveal that the cobalt catalyst is involved in the oxidative addition and carbometalation steps in the reaction, whereas the chromium salt generates highly nucleophilic allylchromium intermediates from allylcobalt species, without the loss of stereochemical information, to allow the addition to aldehydes. Beilstein-Institut 2018-06-11 /pmc/articles/PMC6009127/ /pubmed/29977404 http://dx.doi.org/10.3762/bjoc.14.118 Text en Copyright © 2018, Komeyama et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Komeyama, Kimihiro
Sakiyama, Shunsuke
Iwashita, Kento
Osaka, Itaru
Takaki, Ken
Three-component coupling of aryl iodides, allenes, and aldehydes catalyzed by a Co/Cr-hybrid catalyst
title Three-component coupling of aryl iodides, allenes, and aldehydes catalyzed by a Co/Cr-hybrid catalyst
title_full Three-component coupling of aryl iodides, allenes, and aldehydes catalyzed by a Co/Cr-hybrid catalyst
title_fullStr Three-component coupling of aryl iodides, allenes, and aldehydes catalyzed by a Co/Cr-hybrid catalyst
title_full_unstemmed Three-component coupling of aryl iodides, allenes, and aldehydes catalyzed by a Co/Cr-hybrid catalyst
title_short Three-component coupling of aryl iodides, allenes, and aldehydes catalyzed by a Co/Cr-hybrid catalyst
title_sort three-component coupling of aryl iodides, allenes, and aldehydes catalyzed by a co/cr-hybrid catalyst
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6009127/
https://www.ncbi.nlm.nih.gov/pubmed/29977404
http://dx.doi.org/10.3762/bjoc.14.118
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