%0 Journal Article
%A Cooper, Lisa
%A Alonso Gómez, José Miguel
%A Eagling, Louise
%A Newson, Helen
%A Herath, Sachini
%A Thomson, Christopher
%A Lister, Andrew
%A Howsham, Catherine
%A Cox, Brian
%A Muñoz, María Paz
%T Synthesis of a Novel Type of 2,3’-BIMs via Platinum-Catalysed Reaction of Indolylallenes with Indoles
%D 2018
%@ 0947-6539
%U https://hdl.handle.net/20.500.14352/92592
%X 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.
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