Affiliation:
1. Instituto de Ciências Exatas Departamento de Química Universidade Federal de Minas Gerais – UFMG 31270-901 Belo Horizonte – MG Brazil
2. Department of Chemistry University of Liverpool Crown Street Liverpool L69 7ZD United Kingdom
3. School of Chemistry University of Bristol Cantock's Close Bristol BS8 1TS United Kingdom
4. The Ferrier Research Institute Victoria University of Wellington Wellington 6012 New Zealand
Abstract
AbstractThe 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.
Funder
Conselho Nacional de Desenvolvimento Científico e Tecnológico
Fundação de Amparo à Pesquisa do Estado de Minas Gerais
Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
Alexander von Humboldt-Stiftung
Royal Society of Chemistry