Cobalt-catalyzed nucleophilic addition of the allylic C(sp(3))–H bond of simple alkenes to ketones

We herein describe a cobalt/Xantphos-catalyzed regioselective addition of simple alkenes to acetophenone derivatives, affording branched homoallylic alcohols in high yields with perfect branch selectivities. The intermediate of the reaction would be a nucleophilic allylcobalt(I) species generated vi...

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Autores principales: Mita, Tsuyoshi, Uchiyama, Masashi, Michigami, Kenichi, Sato, Yoshihiro
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2018
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6122116/
https://www.ncbi.nlm.nih.gov/pubmed/30202455
http://dx.doi.org/10.3762/bjoc.14.176
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author Mita, Tsuyoshi
Uchiyama, Masashi
Michigami, Kenichi
Sato, Yoshihiro
author_facet Mita, Tsuyoshi
Uchiyama, Masashi
Michigami, Kenichi
Sato, Yoshihiro
author_sort Mita, Tsuyoshi
collection PubMed
description We herein describe a cobalt/Xantphos-catalyzed regioselective addition of simple alkenes to acetophenone derivatives, affording branched homoallylic alcohols in high yields with perfect branch selectivities. The intermediate of the reaction would be a nucleophilic allylcobalt(I) species generated via cleavage of the low reactive allylic C(sp(3))–H bond of simple terminal alkenes.
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spelling pubmed-61221162018-09-10 Cobalt-catalyzed nucleophilic addition of the allylic C(sp(3))–H bond of simple alkenes to ketones Mita, Tsuyoshi Uchiyama, Masashi Michigami, Kenichi Sato, Yoshihiro Beilstein J Org Chem Letter We herein describe a cobalt/Xantphos-catalyzed regioselective addition of simple alkenes to acetophenone derivatives, affording branched homoallylic alcohols in high yields with perfect branch selectivities. The intermediate of the reaction would be a nucleophilic allylcobalt(I) species generated via cleavage of the low reactive allylic C(sp(3))–H bond of simple terminal alkenes. Beilstein-Institut 2018-08-02 /pmc/articles/PMC6122116/ /pubmed/30202455 http://dx.doi.org/10.3762/bjoc.14.176 Text en Copyright © 2018, Mita 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). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Mita, Tsuyoshi
Uchiyama, Masashi
Michigami, Kenichi
Sato, Yoshihiro
Cobalt-catalyzed nucleophilic addition of the allylic C(sp(3))–H bond of simple alkenes to ketones
title Cobalt-catalyzed nucleophilic addition of the allylic C(sp(3))–H bond of simple alkenes to ketones
title_full Cobalt-catalyzed nucleophilic addition of the allylic C(sp(3))–H bond of simple alkenes to ketones
title_fullStr Cobalt-catalyzed nucleophilic addition of the allylic C(sp(3))–H bond of simple alkenes to ketones
title_full_unstemmed Cobalt-catalyzed nucleophilic addition of the allylic C(sp(3))–H bond of simple alkenes to ketones
title_short Cobalt-catalyzed nucleophilic addition of the allylic C(sp(3))–H bond of simple alkenes to ketones
title_sort cobalt-catalyzed nucleophilic addition of the allylic c(sp(3))–h bond of simple alkenes to ketones
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6122116/
https://www.ncbi.nlm.nih.gov/pubmed/30202455
http://dx.doi.org/10.3762/bjoc.14.176
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AT michigamikenichi cobaltcatalyzednucleophilicadditionoftheallyliccsp3hbondofsimplealkenestoketones
AT satoyoshihiro cobaltcatalyzednucleophilicadditionoftheallyliccsp3hbondofsimplealkenestoketones

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