Hantzsch Ester-Mediated Photochemical Transformations in the Ketone Series: Remote C(sp3)-H Arylation and Cyclopentene Synthesis through Strain Release

Publikationstyp:
Zeitschriftenaufsatz
Metadaten:
Autoren
  • Jan Paternoga
  • Jonas Kuehlborn
  • Nils Ole Rossdam
  • Till Opatz
Autoren-URL
https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000621599900011&DestLinkType=FullRecord&DestApp=WOS_CPL
DOI
10.1021/acs.joc.0c02591
eISSN
1520-6904
Externe Identifier
  • Clarivate Analytics Document Solution ID: QM2GX
  • PubMed Identifier: 33513020
ISSN
0022-3263
Ausgabe der Veröffentlichung
4
Zeitschrift
JOURNAL OF ORGANIC CHEMISTRY
Paginierung
3232 - 3248
Datum der Veröffentlichung
2021
Status
Published
Titel
Hantzsch Ester-Mediated Photochemical Transformations in the Ketone Series: Remote C(sp<SUP>3</SUP>)-H Arylation and Cyclopentene Synthesis through Strain Release
Sub types
  • Article
Ausgabe der Zeitschrift
86

Datenquelle: Web of Science (Lite)

Andere Metadatenquellen:
Autoren
  • Jan Paternoga
  • Jonas Kühlborn
  • Nils Ole Rossdam
  • Till Opatz
DOI
10.1021/acs.joc.0c02591
eISSN
1520-6904
ISSN
0022-3263
Ausgabe der Veröffentlichung
4
Zeitschrift
The Journal of Organic Chemistry
Sprache
en
Online publication date
2021
Paginierung
3232 - 3248
Datum der Veröffentlichung
2021
Status
Published
Herausgeber
American Chemical Society (ACS)
Herausgeber URL
http://dx.doi.org/10.1021/acs.joc.0c02591
Datum der Datenerfassung
2023
Titel
Hantzsch Ester-Mediated Photochemical Transformations in the Ketone Series: Remote C(sp<sup>3</sup>)–H Arylation and Cyclopentene Synthesis through Strain Release
Ausgabe der Zeitschrift
86

Datenquelle: Crossref

Abstract
A metal-free Hantzsch ester-mediated synthesis of cyclopentenylketones as well as γ-hetarylketones starting from ketocyclopropanes under eco-friendly conditions was developed. The versatility of the developed conditions is shown by reacting ketocyclopropanes in both a formal [3 + 2] cycloaddition with terminal alkynes (further investigated using theoretical calculations) and a radical C-C-coupling with cyanopyridines. The newly developed methodologies were later on utilized as a downstream reaction for photogenerated cyclopropanes combining UV and visible light photochemistry. Following this procedure, a UV-driven Norrish-Yang-type reaction induces the ring strain of the intermediates, which serves as activation energy for the subsequent ring transformation.
Addresses
  • Department of Chemistry, Johannes Gutenberg University, Duesbergweg 10-14, 55128 Mainz, Germany.
Autoren
  • Jan Paternoga
  • Jonas Kühlborn
  • Nils Ole Rossdam
  • Till Opatz
DOI
10.1021/acs.joc.0c02591
eISSN
1520-6904
Externe Identifier
  • PubMed Identifier: 33513020
Funding acknowledgements
  • Alliance for High Performance Computing in Rhineland Palatinate:
  • Deutsche Forschungsgemeinschaft: Op90/12-1
Open access
false
ISSN
0022-3263
Ausgabe der Veröffentlichung
4
Zeitschrift
The Journal of organic chemistry
Sprache
eng
Medium
Print-Electronic
Online publication date
2021
Paginierung
3232 - 3248
Datum der Veröffentlichung
2021
Status
Published
Datum der Datenerfassung
2021
Titel
Hantzsch Ester-Mediated Photochemical Transformations in the Ketone Series: Remote C(sp<sup>3</sup>)-H Arylation and Cyclopentene Synthesis through Strain Release.
Sub types
  • Research Support, Non-U.S. Gov't
  • Journal Article
Ausgabe der Zeitschrift
86

Datenquelle: Europe PubMed Central

Abstract
A metal-free Hantzsch ester-mediated synthesis of cyclopentenylketones as well as γ-hetarylketones starting from ketocyclopropanes under eco-friendly conditions was developed. The versatility of the developed conditions is shown by reacting ketocyclopropanes in both a formal [3 + 2] cycloaddition with terminal alkynes (further investigated using theoretical calculations) and a radical C-C-coupling with cyanopyridines. The newly developed methodologies were later on utilized as a downstream reaction for photogenerated cyclopropanes combining UV and visible light photochemistry. Following this procedure, a UV-driven Norrish-Yang-type reaction induces the ring strain of the intermediates, which serves as activation energy for the subsequent ring transformation.
Autoren
  • Jan Paternoga
  • Jonas Kühlborn
  • Nils Ole Rossdam
  • Till Opatz
Autoren-URL
https://www.ncbi.nlm.nih.gov/pubmed/33513020
DOI
10.1021/acs.joc.0c02591
eISSN
1520-6904
Ausgabe der Veröffentlichung
4
Zeitschrift
J Org Chem
Sprache
eng
Country
United States
Paginierung
3232 - 3248
Datum der Veröffentlichung
2021
Status
Published
Titel
Hantzsch Ester-Mediated Photochemical Transformations in the Ketone Series: Remote C(sp3)-H Arylation and Cyclopentene Synthesis through Strain Release.
Sub types
  • Journal Article
  • Research Support, Non-U.S. Gov't
Ausgabe der Zeitschrift
86

Datenquelle: PubMed

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