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Issue 48, 2016
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Visible-light-induced phenylchalcogenyl-oxygenation of allenes having aryl or electron withdrawing substituents with ambient air as a sole oxidant

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Abstract

The synthesis of regio- and stereoselective aryl substituted α,β-unsaturated aldehydes and ketones from activated allenes was achieved. This mild and non-metallic oxidation is exclusively driven by benign ambient air and triggered by visible light. The same starting materials under ideal anaerobic conditions led to the 2,3-diphenylselenation adduct with no trace of oxygenated products, demonstrating dissolved oxygen as a chemical switch for two different reaction pathways. The salient feature of this protocol is the single electron transfer (SET) achieved by irradiation of one of two organic molecules thereby avoiding a sensitizer to form a radical ion pair.

Graphical abstract: Visible-light-induced phenylchalcogenyl-oxygenation of allenes having aryl or electron withdrawing substituents with ambient air as a sole oxidant

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Article information


Submitted
16 Sep 2016
Accepted
11 Nov 2016
First published
11 Nov 2016

Org. Biomol. Chem., 2016,14, 11415-11425
Article type
Paper

Visible-light-induced phenylchalcogenyl-oxygenation of allenes having aryl or electron withdrawing substituents with ambient air as a sole oxidant

G. Kumaraswamy, S. Vijaykumar, K. Ankamma and V. Narayanarao, Org. Biomol. Chem., 2016, 14, 11415
DOI: 10.1039/C6OB02033J

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