Jolley, KE, Chapman, MR and Blacker, AJ orcid.org/0000-0003-4898-2712 (2018) A general and atom-efficient continuous-flow approach to prepare amines, amides and imines via reactive N-chloramines. Beilstein Journal of Organic Chemistry, 14. pp. 2220-2228. ISSN 1860-5397
Abstract
Chloramines are an important class of reagents, providing a convenient source of chlorine or electrophilic nitrogen. However, the instability of these compounds is a problem which makes their isolation and handling difficult. To overcome these hazards, a continuous-flow approach is reported which generates and immediately reacts N-chloramines directly, avoiding purification and isolation steps. 2-Chloramines were produced from the reaction of styrenes with N-alkyl-N-sulfonyl-N-chloramines, whilst N-alkyl or N,N’-dialkyl-N-chloramines reacted with anisaldehyde in the presence of t-BuO₂H oxidant to afford amides. Primary and secondary imines were produced under continuous conditions from the reaction of N-chloramines with base, with one example subsequently reduced under asymmetric conditions to produce a chiral amine in 94% ee.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2018 Jolley et al.; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://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). |
Keywords: | continuous flow; CSTR; N-chloramine; synthetic methods; telescoping |
Dates: |
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Institution: | The University of Leeds |
Academic Units: | The University of Leeds > Faculty of Engineering & Physical Sciences (Leeds) > School of Chemistry (Leeds) > Organic Chemistry (Leeds) |
Funding Information: | Funder Grant number EU - European Union 115360 EU - European Union 115360 EU - European Union 115360 EU - European Union 115360 EU - European Union 115360 EU - European Union 115360 EU - European Union 115360 EU - European Union 115360 |
Depositing User: | Symplectic Publications |
Date Deposited: | 29 Aug 2018 15:36 |
Last Modified: | 29 Aug 2018 15:36 |
Status: | Published |
Publisher: | Beilstein-Institut |
Identification Number: | 10.3762/bjoc.14.196 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:134979 |