The Synthesis and Reactivity of Naphthoquinonynes

de Carvalho, Renato L ORCID: 0000-0002-8515-9306, Wood, James M ORCID: 0000-0002-5965-1006, Almeida, Renata G ORCID: 0000-0003-2896-0487, Berry, Neil G ORCID: 0000-0003-1928-0738, da Silva Júnior, Eufrânio N ORCID: 0000-0003-1281-5453 and Bower, John F ORCID: 0000-0002-7551-8221 (2024) The Synthesis and Reactivity of Naphthoquinonynes. Angewandte Chemie, 136 (18).

Text Manuscript Aryne Project - accepted with no watermarks.docx - Author Accepted Manuscript Available under License Creative Commons Attribution. Download (478kB)

Abstract

<jats:title>Abstract</jats:title><jats:p>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 <jats:italic>while maintaining the integrity of the highly sensitive quinone unit</jats:italic>. 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.</jats:p>

Item Type:	Article
Divisions:	Faculty of Science and Engineering > School of Physical Sciences
Depositing User:	Symplectic Admin
Date Deposited:	21 Mar 2024 09:22
Last Modified:	01 May 2024 23:03
DOI:	10.1002/ange.202400188
Related URLs:	Publisher
URI:	https://livrepository.liverpool.ac.uk/id/eprint/3179757