The Synthesis and Reactivity of Naphthoquinonynes.
Angew Chem Int Ed Engl
; 63(18): e202400188, 2024 Apr 24.
Article
em En
| MEDLINE
| ID: mdl-38445547
ABSTRACT
The first systematic exploration of the synthesis and reactivity of naphthoquinonynes is described. Routes to two regioisomeric Kobayashi-type naphthoquinonyne precursors have been developed, and the reactivity of the ensuing 6,7- and 5,6-aryne intermediates has been investigated. Remarkably, these studies have revealed that a broad range of cycloadditions, nucleophile additions and difunctionalizations can be achieved while maintaining the integrity of the highly sensitive quinone unit. The methodologies offer a powerful diversity oriented approach to C6 and C7 functionalized naphthoquinones, which are typically challenging to access. From a reactivity viewpoint, the study is significant because it demonstrates that aryne-based functionalizations can be utilized strategically in the presence of highly reactive and directly competing functionality.
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MEDLINE
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En
Ano de publicação:
2024
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Article