The Synthesis and Reactivity of Naphthoquinonynes.

de Carvalho, Renato L, Wood, James M, Almeida, Renata G, Berry, Neil G ORCID: 0000-0003-1928-0738, da Silva Júnior, Eufrânio N and Bower, John F ORCID: 0000-0002-7551-8221 (2024) The Synthesis and Reactivity of Naphthoquinonynes. Angewandte Chemie (International ed. in English), 63 (18). e202400188-e202400188. ISSN 1433-7851, 1521-3773

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Official URL: https://doi.org/10.1002/anie.202400188

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.

Item Type:	Article
Uncontrolled Keywords:	arynes, cycloadditions, heterocycles, naphthoquinonyne, quinones
Divisions:	Faculty of Science and Engineering > School of Physical Sciences
Depositing User:	Symplectic Admin
Date Deposited:	16 Apr 2024 10:01
Last Modified:	08 Dec 2024 00:31
DOI:	10.1002/anie.202400188
Open Access URL:	https://doi.org/10.1002/anie.202400188
Related URLs:	Author Publisher
URI:	https://livrepository.liverpool.ac.uk/id/eprint/3180370