Photocatalytic (3 + 2) dipolar cycloadditions of aziridines driven by visible-light.
Chem Sci
; 15(1): 271-277, 2023 Dec 20.
Article
in En
| MEDLINE
| ID: mdl-38131079
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 in situ 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.
Full text:
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Collection:
01-internacional
Database:
MEDLINE
Language:
En
Journal:
Chem Sci
Year:
2023
Type:
Article