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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...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2020
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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. |
format | Online Article Text |
id | pubmed-7187458 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT bielefeldjens fasttitaniumcatalyzedhydroaminomethylationofalkenesandtheformalconversionofmethylamine AT doyesven fasttitaniumcatalyzedhydroaminomethylationofalkenesandtheformalconversionofmethylamine |