Show simple item record

dc.contributor.author
Schuhmacher, Anne
dc.contributor.author
Shiro, Tomoya
dc.contributor.author
Ryan, Sarah J.
dc.contributor.author
Bode, Jeffrey W.
dc.date.accessioned
2021-07-30T11:02:23Z
dc.date.available
2020-08-16T12:16:04Z
dc.date.available
2020-08-18T11:53:00Z
dc.date.available
2021-07-30T11:02:23Z
dc.date.issued
2020-08-07
dc.identifier.issn
2041-6520
dc.identifier.issn
2041-6539
dc.identifier.other
10.1039/d0sc01330g
en_US
dc.identifier.uri
http://hdl.handle.net/20.500.11850/431585
dc.identifier.doi
10.3929/ethz-b-000431585
dc.description.abstract
Although highly effective for most amide syntheses, the activation of carboxylic acids requires the use of problematic coupling reagents and is often poorly suited for challenging cases such as N-methyl amino acids. As an alternative to both secondary and tertiary amides, we report their convenient synthesis by the rapid oxidation of trifluoroborate iminiums (TIMs). TIMs are easily prepared by acid-promoted condensation of potassium acyltrifluoroborates (KATs) and amines and are cleanly and rapidly oxidized to amides with hydrogen peroxide. The overall transformation can be conducted either as a one-pot procedure or via isolation of the TIM. The unique nature of the neutral, zwitterionic TIMs makes possible the preparation of tertiary amides via an iminium species that would not be accessible from other carbonyl derivatives and can be conducted in the presence of unprotected functional groups including acids, alcohols and thioethers. In preliminary studies, this approach was applied to the late-stage modifications of long peptides and the iterative synthesis of short, N-methylated peptides without the need for coupling agents.
en_US
dc.format
application/pdf
en_US
dc.language.iso
en
en_US
dc.publisher
Royal Society of Chemistry
en_US
dc.rights.uri
http://creativecommons.org/licenses/by-nc/3.0/
dc.title
Synthesis of secondary and tertiary amides without coupling agents from amines and potassium acyltrifluoroborates (KATs)
en_US
dc.type
Journal Article
dc.rights.license
Creative Commons Attribution-NonCommercial 3.0 Unported
dc.date.published
2020-03-10
ethz.journal.title
Chemical Science
ethz.journal.volume
11
en_US
ethz.journal.issue
29
en_US
ethz.journal.abbreviated
Chem. Sci.
ethz.pages.start
7609
en_US
ethz.pages.end
7614
en_US
ethz.size
6 p.
en_US
ethz.version.deposit
publishedVersion
en_US
ethz.identifier.scopus
ethz.publication.place
Cambridge
en_US
ethz.publication.status
published
en_US
ethz.leitzahl
ETH Zürich::00002 - ETH Zürich::00012 - Lehre und Forschung::00007 - Departemente::02020 - Dep. Chemie und Angewandte Biowiss. / Dep. of Chemistry and Applied Biosc.::02514 - Laboratorium für Organische Chemie / Laboratory of Organic Chemistry::03861 - Bode, Jeffrey W. / Bode, Jeffrey W.
en_US
ethz.leitzahl.certified
ETH Zürich::00002 - ETH Zürich::00012 - Lehre und Forschung::00007 - Departemente::02020 - Dep. Chemie und Angewandte Biowiss. / Dep. of Chemistry and Applied Biosc.::02514 - Laboratorium für Organische Chemie / Laboratory of Organic Chemistry::03861 - Bode, Jeffrey W. / Bode, Jeffrey W.
ethz.date.deposited
2020-08-16T12:16:12Z
ethz.source
SCOPUS
ethz.eth
yes
en_US
ethz.availability
Open access
en_US
ethz.rosetta.installDate
2020-08-18T11:53:15Z
ethz.rosetta.lastUpdated
2021-02-15T16:34:09Z
ethz.rosetta.exportRequired
true
ethz.rosetta.versionExported
true
ethz.COinS
ctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.atitle=Synthesis%20of%20secondary%20and%20tertiary%20amides%20without%20coupling%20agents%20from%20amines%20and%20potassium%20acyltrifluoroborates%20(KATs)&rft.jtitle=Chemical%20Science&rft.date=2020-08-07&rft.volume=11&rft.issue=29&rft.spage=7609&rft.epage=7614&rft.issn=2041-6520&2041-6539&rft.au=Schuhmacher,%20Anne&Shiro,%20Tomoya&Ryan,%20Sarah%20J.&Bode,%20Jeffrey%20W.&rft.genre=article&rft_id=info:doi/10.1039/d0sc01330g&
 Search print copy at ETH Library

Files in this item

Thumbnail

Publication type

Show simple item record