Visible Light Driven Hydro-/Deuterodefunctionalization of Anilines

Majek, Michal and Filace, Fabiana and Jacobi von Wangelin, Axel (2015) Visible Light Driven Hydro-/Deuterodefunctionalization of Anilines. CHEMISTRY-A EUROPEAN JOURNAL, 21 (12). pp. 4518-4522. ISSN 0947-6539, 1521-3765

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Abstract

The defunctionalization of anilines is an important strategy in aromatic-substitution chemistry. Herein, we report on visible light mediated hydro- and deuterodediazonations in solutions of DMF. The mild reaction conditions (DMF, RT, no additives) tolerate various functional groups and allow the site-specific introduction of D atoms to the arene. Mechanistic investigations indicate the participation of photoredox and radical chain pathways and competing abstraction of methyl and formyl hydrogen atoms from DMF.

Item Type: Article
Uncontrolled Keywords: ARYL DIAZONIUM SALTS; PHOTOREDOX CATALYSIS; REDUCTIVE DEAMINATION; ORGANIC-SYNTHESIS; METAL-FREE; EOSIN Y; DERIVATIVES; AMINES; HYDRODEDIAZONIATION; PROTODEDIAZONIATION; defunctionalization; organocatalysis; photocatalysis; radical reactions
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Prof. Dr. Axel Jacobi von Wangelin
Depositing User: Dr. Gernot Deinzer
Date Deposited: 22 Jul 2019 14:10
Last Modified: 22 Jul 2019 14:10
URI: https://pred.uni-regensburg.de/id/eprint/5783

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