Photocatalytic generation of highly reactive alkynes under visible light conditions | 8/1/2019 | Staff
urbanpatrioturbanpatriot (Posted by) Level 4
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Alkynes are a group of organic compounds that are used to manufacture industrial reagents and polymers. Photolysis of a cyclopropenone with UV-light is a useful method to generate a highly reactive alkyne. However, if the reaction mix contains accompanying compounds that are sensitive to UV light, they will degenerate. Therefore, performing this reaction in the presence of visible light instead will keep such compounds intact. A research team at Kanazawa University has identified catalysts that can facilitate the photolysis of visible-light-stable cyclopropenones under visible-light conditions.

The team first screened a panel of six potential catalysts to identify those yielding the highest proportion of aminoalkynes from aminocyclopropenones in the presence of visible light. To assess this, a phototriggered dehydration condensation reaction was set up. This is one of the few reactions wherein the aminoalkyne synthesized from the aminocyclopropenone directly undergoes a series of intermediate steps to yield chemical compounds known as amides.

Reaction - Mixture - Household - Fluorescence - Lamp

When this reaction mixture was irradiated with a household fluorescence lamp, two catalysts showed the highest yield of the amide. In the presence of these two catalysts more than 90% of the cyclopropenone was consumed, suggestive of their efficiency under visible light. These observations were not seen under dark conditions, further suggesting the dependence of these two catalysts on light within the visible spectrum. Interestingly,...
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