The Synthesis and Reactivity of Naphthoquinonynes.

de Carvalho, Renato L.; Wood, James M.; Almeida, Renata G.; Berry, Neil G.; da Silva Júnior, Eufrânio N.; Bower, John F.

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.

RING formation (Chemistry); HETEROCYCLIC compounds; QUINONE

Angewandte Chemie, 2024, Vol 136, Issue 18, p1

0044-8249

Academic Journal

10.1002/ange.202400188