Visible-light photocatalytic metal-free multicomponent Ugi-like chemistry

The possibility of harnessing the photoactivity of isocyanides in the development of metal-free Ugi-like visible light photo-triggered multicomponent transformations has been reported herein. More in detail, Ugi-3CR, Ugi-Tetrazole-3CR, and UgiJoulli-3CR afforded imide peptidomimetic derivatives in g...

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Veröffentlicht in:Green chemistry : an international journal and green chemistry resource : GC 2022-05, Vol.24 (1), p.3993-43
Hauptverfasser: Russo, Camilla, Graziani, Giulia, Cannalire, Rolando, Tron, Gian Cesare, Giustiniano, Mariateresa
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Sprache:eng
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Zusammenfassung:The possibility of harnessing the photoactivity of isocyanides in the development of metal-free Ugi-like visible light photo-triggered multicomponent transformations has been reported herein. More in detail, Ugi-3CR, Ugi-Tetrazole-3CR, and UgiJoulli-3CR afforded imide peptidomimetic derivatives in good yields and with a wide substrate scope, involving the late-stage editing of complex bioactive scaffolds. Furthermore, a 2-step-one-pot sequence affording linear secondary imides, and a 3-step-one-pot protocol leading to densely functionalized bis-amide derivatives have also been developed to highlight the huge potential of these mild metal-free reaction conditions to afford complex and diverse compounds while being in accordance with the green chemistry principles . The direct photoexcitation of isocyanides is able to trigger a collection of Ugi-like multicomponent reactions under metal-free conditions and in the absence of any additives starting from both linear and cyclic tertiary aromatic amines.
ISSN:1463-9262
1463-9270
DOI:10.1039/d2gc00855f