Visible-Light-Promoted Generation of alpha-Ketoradicals from Vinyl-bromides and Molecular Oxygen: Synthesis of Indenones and Dihydroindeno[1,2-c]chromenes

Pagire, Santosh K. and Kreitmeier, Peter and Reiser, Oliver (2017) Visible-Light-Promoted Generation of alpha-Ketoradicals from Vinyl-bromides and Molecular Oxygen: Synthesis of Indenones and Dihydroindeno[1,2-c]chromenes. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 56 (36). pp. 10928-10932. ISSN 1433-7851, 1521-3773

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Abstract

Ortho-alkynylated alpha-bromocinnamates can be converted by a visible-light-mediated photocascade reaction with molecular oxygen into either indenones or dihydroindeno[1,2-c]chromenes. The one-step process features key photochemical steps, that is, the initial activation of vinyl bromides through energy transfer to give alpha-ketoradicals in a reaction with molecular oxygen, followed by alpha-oxidation of an arene moiety by 6-pi electrocyclization, and subsequent hydroxylation by an electron-transfer process from the same photocatalyst leads to the dihydroindeno[1,2-c]chromenes.

Item Type: Article
Uncontrolled Keywords: PHOTOREDOX CATALYSIS; RING-CLOSURE; PHOTOCHEMICAL-SYNTHESIS; ORGANIC-SYNTHESIS; ENERGY-TRANSFER; SINGLE-LAYER; PHOTOCATALYSIS; CYCLIZATIONS; COMPLEX; ALKYNES; dioxygen activation; indenones; photocascades; taiwaniaquinoids; alpha-ketoradicals
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser
Depositing User: Dr. Gernot Deinzer
Date Deposited: 14 Dec 2018 13:15
Last Modified: 11 Feb 2019 14:33
URI: https://pred.uni-regensburg.de/id/eprint/1362

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