2026-06-27T16:19:26Zhttps://docta.ucm.es/rest/oai/request

oai:docta.ucm.es:20.500.14352/925922025-03-18T14:05:13Zcom_20.500.14352_14col_20.500.14352_15

Cooper, Lisa Alonso Gómez, José Miguel Eagling, Louise Newson, Helen Herath, Sachini Thomson, Christopher Lister, Andrew Howsham, Catherine Cox, Brian Muñoz, María Paz 2024-01-11T15:53:09Z 2024-01-11T15:53:09Z 2018 L. Cooper, J. M. Alonso, L. Eagling, H. Newson, S. Herath, C. Thomson, A. Lister, C. Howsham, B. Cox, M. P. Muñoz, Chem. Eur. J. 2018, 24, 6105. 0947-6539 10.1002/chem.201705417 https://hdl.handle.net/20.500.14352/92592 https://doi.org/10.1002/chem.201705417 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. eng open access Synthesis of a Novel Type of 2,3’-BIMs via Platinum-Catalysed Reaction of Indolylallenes with Indoles journal article