Synthesis of a novel type of 2,3'-BIMs via platinum-catalysed reaction of indolylallenes with indoles

Cooper, Lisa, Alonso, José Miguel, Eagling, Louise, Newson, Helen, Herath, Sachini, Thomson, Christopher, Lister, Andrew, Howsham, Catherine, Cox, Brian and Paz Muñoz, María ORCID: https://orcid.org/0000-0001-9037-349X (2018) Synthesis of a novel type of 2,3'-BIMs via platinum-catalysed reaction of indolylallenes with indoles. Chemistry - A European Journal, 24 (23). pp. 6105-6114. ISSN 0947-6539

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Abstract

Optimisation, scope and mechanism of the platinum-catalysed addition of indoles to indolylallenes is reported here to give 2,3'-BIMs with a novel core structure very relevant for pharmaceutical industry. The reaction is modulated by the electronic properties of the substituents on both indoles, with the 2,3'-BIMs favoured when electron donating groups are present. Although simple at first, a complex mechanism has been uncovered that explains the different behaviour of these systems with platinum when compared with other metals (e.g. gold). Detailed labelling studies have shown Pt-catalysed 6-endo-trig cyclisation of the indollylallene as the first step of the reaction and the involvement of two cyclic vinyl-platinum intermediates in equilibrium through a platinum carbene, as the key intermediates of the catalytic cycle towards the second nucleophilic attack and formation of the BIMs.

Item Type: Article
Uncontrolled Keywords: platinum,allene,indole,bisindolylmethane,mechanism
Faculty \ School: Faculty of Science > School of Chemistry
Depositing User: Pure Connector
Date Deposited: 02 Feb 2018 15:30
Last Modified: 23 Sep 2022 18:30
URI: https://ueaeprints.uea.ac.uk/id/eprint/66212
DOI: 10.1002/chem.201705417

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