Person:
Alonso Gómez, José Miguel

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First Name
José Miguel
Last Name
Alonso Gómez
URI
https://hdl.handle.net/20.500.14352/76150
Affiliation
Universidad Complutense de Madrid
Faculty / Institute
Ciencias Químicas
Department
Química Orgánica
Area
Química Orgánica
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Author: Herath, Sachini × Subject: 544 ×

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    Synthesis of a Novel Type of 2,3’-BIMs via Platinum-Catalysed Reaction of Indolylallenes with Indoles
    (Chemistry A European Journal, 2018) Cooper, Lisa; Alonso Gómez, José Miguel; Eagling, Louise; Newson, Helen; Herath, Sachini; Thomson, Christopher; Lister, Andrew; Howsham, Catherine; Cox, Brian; Muñoz, María Paz
    Optimisation, scope and mechanism of the platinum catalysed addition of indoles to indollylallenes is reported here to give 2,3-BIMs with a novel core structure very relevant for pharmaceutical industry. The reaction is modulated by 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.