AI Article Synopsis
- A new reaction method called (3 + 2) cycloaddition was developed using an organic photocatalyst and visible light, allowing for very fast reactions in just a few minutes and achieving nearly complete atom economy.
- The process utilizes various aziridines and dipolarophiles, demonstrating impressive yields and good selectivity across 28 examples.
- Mechanistic studies suggest the reaction works through two electron-transfer steps, and an aerobic cascade process can produce a variety of pyrrole derivatives with notable optical properties that can be used to monitor the efficacy of the reaction.
Article Abstract
Herein, we document the design and development of a novel (3 + 2) cycloaddition reaction aided by the activity of an organic photocatalyst and visible light. The process is extremely fast, taking place in a few minutes, with virtually complete atom economy. A large variety of structurally diverse aziridines were used as masked ylides in the presence of different types of dipolarophiles (28 examples with up to 94% yield and >95 : 5 dr). Mechanistic insights obtained from photophysical, electrochemical and experimental studies highlight that the chemistry is driven by the generation of the reactive ylide through two consecutive electron-transfer processes. We also report an aerobic cascade process, where an additional oxidation step grants access to a vast array of pyrrole derivatives (19 examples with up to 95% yield). Interestingly, the extended aromatic core exhibits a distinctive absorption and emission profile, which can be easily used to tag the effectiveness of this covalent linkage.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10732004 | PMC |
| http://dx.doi.org/10.1039/d3sc05997a | DOI Listing |
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Article Synopsis
- A new reaction method called (3 + 2) cycloaddition was developed using an organic photocatalyst and visible light, allowing for very fast reactions in just a few minutes and achieving nearly complete atom economy.
- The process utilizes various aziridines and dipolarophiles, demonstrating impressive yields and good selectivity across 28 examples.
- Mechanistic studies suggest the reaction works through two electron-transfer steps, and an aerobic cascade process can produce a variety of pyrrole derivatives with notable optical properties that can be used to monitor the efficacy of the reaction.
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