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Reductive Amination by Photoredox Catalysis and Polarity-Matched Hydrogen Atom Transfer

Guo, Xingwei and Wenger, Oliver S.. (2018) Reductive Amination by Photoredox Catalysis and Polarity-Matched Hydrogen Atom Transfer. Angewandte Chemie International Edition, 57 (9). pp. 2469-2473.

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Abstract

The excitation of a RuII photosensitizer in the presence of ascorbic acid leads to the reduction of iminium ions to electron‐rich α‐aminoalkyl radical intermediates, which are rapidly converted into reductive amination products by thiol‐mediated hydrogen atom transfer (HAT). As a result, the reductive amination of carbonyl compounds with amines by photoredox catalysis proceeds in good to excellent yields and with broad substrate scope and good functional group tolerance. The three key features of this work are 1) the rapid interception of electron‐rich α‐aminoalkyl radical intermediates by polarity‐matched HAT in a photoredox reaction, 2) the method of reductive amination by photoredox catalysis itself, and 3) the application of this new method for temporally and spatially controlled reactions on a solid support, as demonstrated by the attachment of a fluorescent dye on an activated cellulose support by photoredox‐catalyzed reductive amination.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Anorganische Chemie (Wenger)
UniBasel Contributors:Wenger, Oliver and Guo, Xingwei
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Wiley
ISSN:1433-7851
e-ISSN:1521-3773
Note:Publication type according to Uni Basel Research Database: Journal article -- The final publication is available at Wiley, see DOI link
Language:English
Identification Number:
Last Modified:11 Jun 2018 12:39
Deposited On:11 Jun 2018 12:39

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