Green-Light Photocatalysis: Borylated Benzo[c][1,2,5]thiadiazole (BTZ) Enables Phosphorylation of Quinoline Derivatives
Leonardo Amicosante, Dominic Taylor, Luca Craciunescu, Andrew W. Prentice, Adilet Zhakeyev, Bence Szabó, Georgina M. Rosair, Martin J. Paterson, Scott J. Dalgarno, Filipe Vilela
TL;DR
Scientists developed new green-light photocatalysts that efficiently phosphorylate quinoline compounds, enabling streamlined antibacterial drug production.
Contribution
A novel library of green-light-responsive photocatalysts enables efficient phosphorylation and automated synthesis of antibacterial compounds.
Findings
The new photocatalysts achieved up to 73% conversion in phosphorylation under recycle flow conditions.
A dual photocatalyst system enabled a two-step phosphorylation and Minisci coupling process for antibacterial compound synthesis.
The process uses low-energy green light and inexpensive starting materials for streamlined drug production.
Abstract
A library of 10 novel organophotocatalysts (ORG-PRCs) has been prepared by the one-pot, two-step ortho-borylation of 4,7-diarylbenzo[c][1,2,5]thiadiazoles (BTZs). The borylation reaction was accompanied by a substantial bathochromic shift in both the absorption and emission spectra (up to 142 nm), allowing these photocatalysts to operate using low-energy green light instead of the high-energy near-UV light that BTZ photocatalysts typically require. The library of photocatalysts was tested using the phosphorylation of quinoline compounds under both batch and recycle flow conditions, achieving up to 40 and 73% conversion, respectively, in 4 h. The versatility of the recycle flow system was further tested by developing a sequential two-step phosphorylation followed by a Minisci coupling procedure using a dual photocatalyst system. This allowed automated production of the target…
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Taxonomy
TopicsRadical Photochemical Reactions · Sulfur-Based Synthesis Techniques · Catalytic C–H Functionalization Methods