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Synthesis of β‐Diamine Building Blocks by Photocatalytic Hydroamination of Enecarbamates with Amines, Ammonia and N−H Heterocycles

3‐Amino‐substituted saturated nitrogen heterocycles are an important subclass of β‐diamines, appearing in a number of clinical agents. Herein, we report a unified approach to these products based upon the regioselective photoredox‐mediated hydroamination of enecarbamates. The amine coupling partner...

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Detalles Bibliográficos
Autores principales: Francis, Daniel, Nelson, Adam, Marsden, Stephen P.
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/PMC7756410/
https://www.ncbi.nlm.nih.gov/pubmed/32853417
http://dx.doi.org/10.1002/chem.202003562
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author Francis, Daniel
Nelson, Adam
Marsden, Stephen P.
author_facet Francis, Daniel
Nelson, Adam
Marsden, Stephen P.
author_sort Francis, Daniel
collection PubMed
description 3‐Amino‐substituted saturated nitrogen heterocycles are an important subclass of β‐diamines, appearing in a number of clinical agents. Herein, we report a unified approach to these products based upon the regioselective photoredox‐mediated hydroamination of enecarbamates. The amine coupling partner can encompass diverse amine types under a single set of reaction conditions, including primary alkyl amines, ammonia, aryl and heteroaryl amines, and N−H heterocycles. The method enables the synthesis of a wide range of pharmaceutically relevant building blocks.
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spelling pubmed-77564102020-12-28 Synthesis of β‐Diamine Building Blocks by Photocatalytic Hydroamination of Enecarbamates with Amines, Ammonia and N−H Heterocycles Francis, Daniel Nelson, Adam Marsden, Stephen P. Chemistry Communications 3‐Amino‐substituted saturated nitrogen heterocycles are an important subclass of β‐diamines, appearing in a number of clinical agents. Herein, we report a unified approach to these products based upon the regioselective photoredox‐mediated hydroamination of enecarbamates. The amine coupling partner can encompass diverse amine types under a single set of reaction conditions, including primary alkyl amines, ammonia, aryl and heteroaryl amines, and N−H heterocycles. The method enables the synthesis of a wide range of pharmaceutically relevant building blocks. John Wiley and Sons Inc. 2020-10-07 2020-11-20 /pmc/articles/PMC7756410/ /pubmed/32853417 http://dx.doi.org/10.1002/chem.202003562 Text en © 2020 The Authors. Published by Wiley-VCH GmbH This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Francis, Daniel
Nelson, Adam
Marsden, Stephen P.
Synthesis of β‐Diamine Building Blocks by Photocatalytic Hydroamination of Enecarbamates with Amines, Ammonia and N−H Heterocycles
title Synthesis of β‐Diamine Building Blocks by Photocatalytic Hydroamination of Enecarbamates with Amines, Ammonia and N−H Heterocycles
title_full Synthesis of β‐Diamine Building Blocks by Photocatalytic Hydroamination of Enecarbamates with Amines, Ammonia and N−H Heterocycles
title_fullStr Synthesis of β‐Diamine Building Blocks by Photocatalytic Hydroamination of Enecarbamates with Amines, Ammonia and N−H Heterocycles
title_full_unstemmed Synthesis of β‐Diamine Building Blocks by Photocatalytic Hydroamination of Enecarbamates with Amines, Ammonia and N−H Heterocycles
title_short Synthesis of β‐Diamine Building Blocks by Photocatalytic Hydroamination of Enecarbamates with Amines, Ammonia and N−H Heterocycles
title_sort synthesis of β‐diamine building blocks by photocatalytic hydroamination of enecarbamates with amines, ammonia and n−h heterocycles
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7756410/
https://www.ncbi.nlm.nih.gov/pubmed/32853417
http://dx.doi.org/10.1002/chem.202003562
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