Abstract
We report an acridium-based organic photocatalyst as an efficient replacement for iridium-based photocatalysts to oxidise boronic acid derivatives by a single electron process. Furthermore, we applied the developed catalytic system to the synthesis of four active pharmaceutical ingredients (APIs). A straightforward scale up approach using continuous flow photoreactors is also reported affording gram an hour throughput.
Highlights
We report an acridium-based organic photocatalyst as an efficient replacement for iridium-based photocatalysts to oxidise boronic acid derivatives by a single electron process
A large number of applications have emerged for the catalytic generation of carbon radical species via single electron oxidation of charged anionic species, such as carboxylates, silicates, and trifluoroborate salts.[2]
Despite the promises offered by the photoredox disconnections for pharmaceutical products synthesis,[4] industry has to comply with residual transition metal limits in final products.[5]
Summary
We report an acridium-based organic photocatalyst as an efficient replacement for iridium-based photocatalysts to oxidise boronic acid derivatives by a single electron process. As Mes-Acr-4 consistently led to the highest yields (similar to Ir-1 and Ir-2) with both the boronic ester (1, entry 4) and acid (2, entry 9), it was chosen as a promising replacement to the iridium-based photocatalysts.
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