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Angew Chem Int Ed Engl. 2017 Aug 28;56(36):10928-10932. doi: 10.1002/anie.201702953. Epub 2017 Jul 28.

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

Author information

1
Institut für Organische Chemie, Universität Regensburg, Universitätsstraße 31, 93053, Regensburg, Germany.

Abstract

Ortho-alkynylated α-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 α-ketoradicals in a reaction with molecular oxygen, followed by α-oxidation of an arene moiety by 6-π electrocyclization, and subsequent hydroxylation by an electron-transfer process from the same photocatalyst leads to the dihydroindeno[1,2-c]chromenes.

KEYWORDS:

dioxygen activation; indenones; photocascades; taiwaniaquinoids; α-ketoradicals

PMID:
28621913
DOI:
10.1002/anie.201702953

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