Photochemical ?-Aminonitrile Synthesis Using Zn-Phthalocyaninesas Near-Infrared Photocatalysts
- Publication type:
- Journal article
- Metadata:
-
- Autoren
- Caroline Grundke
- Rodrigo C Silva
- Winald R Kitzmann
- Katja Heinze
- Kleber T de Oliveira
- Till Opatz
- Autoren-URL
- https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000818662400016&DestLinkType=FullRecord&DestApp=WOS_CPL
- DOI
- 10.1021/acs.joc.1c03101
- eISSN
- 1520-6904
- Externe Identifier
- Clarivate Analytics Document Solution ID: 2N8ZX
- PubMed Identifier: 35421314
- ISSN
- 0022-3263
- Ausgabe der Veröffentlichung
- 9
- Zeitschrift
- JOURNAL OF ORGANIC CHEMISTRY
- Paginierung
- 5630 - 5642
- Datum der Veröffentlichung
- 2022
- Status
- Published
- Titel
- Photochemical <i>?</i>-Aminonitrile Synthesis Using Zn-Phthalocyaninesas Near-Infrared Photocatalysts
- Sub types
- Article
- Ausgabe der Zeitschrift
- 87
Data source: Web of Science (Lite)
- Other metadata sources:
-
- Autoren
- Caroline Grundke
- Rodrigo C Silva
- Winald R Kitzmann
- Katja Heinze
- Kleber T de Oliveira
- Till Opatz
- DOI
- 10.1021/acs.joc.1c03101
- eISSN
- 1520-6904
- ISSN
- 0022-3263
- Ausgabe der Veröffentlichung
- 9
- Zeitschrift
- The Journal of Organic Chemistry
- Sprache
- en
- Online publication date
- 2022
- Paginierung
- 5630 - 5642
- Datum der Veröffentlichung
- 2022
- Status
- Published
- Herausgeber
- American Chemical Society (ACS)
- Herausgeber URL
- http://dx.doi.org/10.1021/acs.joc.1c03101
- Datum der Datenerfassung
- 2023
- Titel
- Photochemical α-Aminonitrile Synthesis Using Zn-Phthalocyanines as Near-Infrared Photocatalysts
- Ausgabe der Zeitschrift
- 87
Data source: Crossref
- Abstract
- While photochemical transformations with sunlight almost exclusively utilize the UV-vis part of the solar spectrum, the majority of the photons emitted by the sun have frequencies in the near-infrared region. Phthalocyanines show high structural similarity to the naturally occurring light-harvesting porphyrins, chlorins, and mainly bacteriochlorins and are also known for being efficient and affordable near-infrared light absorbers as well as triplet sensitizers for the production of singlet oxygen. Although having been neglected for a long time in synthetic organic chemistry due to their low solubility and high tendency toward aggregation, their unique photophysical properties and chemical robustness make phthalocyanines attractive photocatalysts for the application in near-infrared-light-driven synthesis strategies. Herein, we report a cheap, simple, and efficient photocatalytic protocol, which is easily scalable under continuous-flow conditions. Various phthalocyanines were studied as near-infrared photosensitizers in oxidative cyanations of tertiary amines to generate α-aminonitriles, a synthetically versatile compound class.
- Addresses
- Department of Chemistry, Johannes Gutenberg University, 55128 Mainz, Germany.
- Autoren
- Caroline Grundke
- Rodrigo C Silva
- Winald R Kitzmann
- Katja Heinze
- Kleber T de Oliveira
- Till Opatz
- DOI
- 10.1021/acs.joc.1c03101
- eISSN
- 1520-6904
- Externe Identifier
- PubMed Identifier: 35421314
- Funding acknowledgements
- Funda????o de Amparo ?? Pesquisa do Estado de S??o Paulo: 2018/00879-6
- Funda????o de Amparo ?? Pesquisa do Estado de S??o Paulo: 2020/06874-6
- Conselho Nacional de Pesquisa: 303890/2019-3
- German Federal Ministry of Education and Research: 01DG17013
- Deutsche Forschungsgemeinschaft: INST 247/1018-1 FUGG
- Funda????o de Amparo ?? Pesquisa do Estado de S??o Paulo: 2019/27176-8
- Conselho Nacional de Pesquisa: 407990/2018-6
- Fonds of the Chemical Industry:
- Coordena????o de Aperfei??oamento de Pessoal de N??vel Superior: 001
- Open access
- false
- ISSN
- 0022-3263
- Ausgabe der Veröffentlichung
- 9
- Zeitschrift
- The Journal of organic chemistry
- Schlüsselwörter
- Zinc Compounds
- Organometallic Compounds
- Indoles
- Photosensitizing Agents
- Isoindoles
- Sprache
- eng
- Medium
- Print-Electronic
- Online publication date
- 2022
- Paginierung
- 5630 - 5642
- Datum der Veröffentlichung
- 2022
- Status
- Published
- Datum der Datenerfassung
- 2022
- Titel
- Photochemical α-Aminonitrile Synthesis Using Zn-Phthalocyanines as Near-Infrared Photocatalysts.
- Sub types
- Research Support, Non-U.S. Gov't
- Journal Article
- Ausgabe der Zeitschrift
- 87
Data source: Europe PubMed Central
- Abstract
- While photochemical transformations with sunlight almost exclusively utilize the UV-vis part of the solar spectrum, the majority of the photons emitted by the sun have frequencies in the near-infrared region. Phthalocyanines show high structural similarity to the naturally occurring light-harvesting porphyrins, chlorins, and mainly bacteriochlorins and are also known for being efficient and affordable near-infrared light absorbers as well as triplet sensitizers for the production of singlet oxygen. Although having been neglected for a long time in synthetic organic chemistry due to their low solubility and high tendency toward aggregation, their unique photophysical properties and chemical robustness make phthalocyanines attractive photocatalysts for the application in near-infrared-light-driven synthesis strategies. Herein, we report a cheap, simple, and efficient photocatalytic protocol, which is easily scalable under continuous-flow conditions. Various phthalocyanines were studied as near-infrared photosensitizers in oxidative cyanations of tertiary amines to generate α-aminonitriles, a synthetically versatile compound class.
- Autoren
- Caroline Grundke
- Rodrigo C Silva
- Winald R Kitzmann
- Katja Heinze
- Kleber T de Oliveira
- Till Opatz
- Autoren-URL
- https://www.ncbi.nlm.nih.gov/pubmed/35421314
- DOI
- 10.1021/acs.joc.1c03101
- eISSN
- 1520-6904
- Ausgabe der Veröffentlichung
- 9
- Zeitschrift
- J Org Chem
- Schlüsselwörter
- Indoles
- Isoindoles
- Organometallic Compounds
- Photosensitizing Agents
- Zinc Compounds
- Sprache
- eng
- Country
- United States
- Paginierung
- 5630 - 5642
- Datum der Veröffentlichung
- 2022
- Status
- Published
- Datum, an dem der Datensatz öffentlich gemacht wurde
- 2022
- Titel
- Photochemical α-Aminonitrile Synthesis Using Zn-Phthalocyanines as Near-Infrared Photocatalysts.
- Sub types
- Journal Article
- Research Support, Non-U.S. Gov't
- Ausgabe der Zeitschrift
- 87
Data source: PubMed
- Beziehungen:
-