Visible light mediated deoxygenations

Published on September 10, 2014

We introduce here a protocol for deoxygenation of alcohols by photoredoxcatalysis with visible light, which allows the recycling of the activating agent under redoxneutral conditions.

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About 60 % of all biomass on earth are carbohydrates, i.e. polyhydroxylated compounds. Removing these hydroxyl groups would be desirable to arrive at compounds that might be used as biofuels or that might be further functionalized by chemistry that has been established in the last century based on fossil starting materials (oil and gas). Chemical deoxygenations however are difficult due to the high stability of the carbon-oxygen bond, which requires activation that in turn produce waste in (over)stoichiometric amounts that cannot be easily recycled. We introduce here a protocol for deoxygenation of alcohols by photoredoxcatalysis with visible light, which allows the recycling of the activating agent under redoxneutral conditions. Moreover, in situ activation and deoxygenation is possible in a flow setup, being attractive for large-scale applications.

Reiser Group | University of Regensburg, Germany

Oliver Reiser teaches Organic Chemistry at the University of Regensburg. He is heading a research group of approx. 25 master and PhD students, developing methods in synthesis and catalysis and their application to natural product, drugs and fine chemical synthesis. His group has published more than 200 research papers.

Daniel Rackl has studied Chemistry at the Universities of Regensburg and Fayetteville/Arkansas and is currently conducting his PhD studies in the group of Oliver Reiser.

Sources

Rackl, D., Kais, V.; Kreitmeier, P.; Reiser, O., Visible light photoredox-catalyzed deoxygenation of alcohols, Beilstein J. Org. Chem. 2014, 10, 2157–2165, DOI: 10.3762/bjoc.10.223.

Rackl, D., Kais, V.; Kreitmeier, P.; Reiser, O., Visible light photoredox-catalyzed deoxygenation of alcohols, Beilstein J. Org. Chem. 2014, 10, 2157–2165, DOI: 10.3762/bjoc.10.223.

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