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Fast Titanium‐Catalyzed Hydroaminomethylation of Alkenes and the Formal Conversion of Methylamine

The scientific interest in catalytic hydroaminoalkylation reactions of alkenes has vastly increased over the past decade, but these reactions have struggled to become a viable option for general laboratory or industrial use because of reaction times of several days. The titanium‐based catalytic syst...

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Detalles Bibliográficos
Autores principales: Bielefeld, Jens, Doye, Sven
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7187458/
https://www.ncbi.nlm.nih.gov/pubmed/31994302
http://dx.doi.org/10.1002/anie.202001111
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author Bielefeld, Jens
Doye, Sven
author_facet Bielefeld, Jens
Doye, Sven
author_sort Bielefeld, Jens
collection PubMed
description The scientific interest in catalytic hydroaminoalkylation reactions of alkenes has vastly increased over the past decade, but these reactions have struggled to become a viable option for general laboratory or industrial use because of reaction times of several days. The titanium‐based catalytic system introduced in this work not only reduces the reaction time by several orders of magnitude, into the range of minutes, but the catalyst is also demonstrated to be easily available from common starting materials, at a cost of approximately 1 € per millimole of catalyst. We were also able to formally perform C−H activation of methylamine and achieve coupling to a broad variety of alkenes, through silyl protection of the amine and simple deprotection by water.
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spelling pubmed-71874582020-04-29 Fast Titanium‐Catalyzed Hydroaminomethylation of Alkenes and the Formal Conversion of Methylamine Bielefeld, Jens Doye, Sven Angew Chem Int Ed Engl Research Articles The scientific interest in catalytic hydroaminoalkylation reactions of alkenes has vastly increased over the past decade, but these reactions have struggled to become a viable option for general laboratory or industrial use because of reaction times of several days. The titanium‐based catalytic system introduced in this work not only reduces the reaction time by several orders of magnitude, into the range of minutes, but the catalyst is also demonstrated to be easily available from common starting materials, at a cost of approximately 1 € per millimole of catalyst. We were also able to formally perform C−H activation of methylamine and achieve coupling to a broad variety of alkenes, through silyl protection of the amine and simple deprotection by water. John Wiley and Sons Inc. 2020-03-02 2020-04-06 /pmc/articles/PMC7187458/ /pubmed/31994302 http://dx.doi.org/10.1002/anie.202001111 Text en © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Research Articles
Bielefeld, Jens
Doye, Sven
Fast Titanium‐Catalyzed Hydroaminomethylation of Alkenes and the Formal Conversion of Methylamine
title Fast Titanium‐Catalyzed Hydroaminomethylation of Alkenes and the Formal Conversion of Methylamine
title_full Fast Titanium‐Catalyzed Hydroaminomethylation of Alkenes and the Formal Conversion of Methylamine
title_fullStr Fast Titanium‐Catalyzed Hydroaminomethylation of Alkenes and the Formal Conversion of Methylamine
title_full_unstemmed Fast Titanium‐Catalyzed Hydroaminomethylation of Alkenes and the Formal Conversion of Methylamine
title_short Fast Titanium‐Catalyzed Hydroaminomethylation of Alkenes and the Formal Conversion of Methylamine
title_sort fast titanium‐catalyzed hydroaminomethylation of alkenes and the formal conversion of methylamine
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7187458/
https://www.ncbi.nlm.nih.gov/pubmed/31994302
http://dx.doi.org/10.1002/anie.202001111
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