RT Journal Article
T1 Synthesis of a Novel Type of 2,3’-BIMs via Platinum-Catalysed Reaction of Indolylallenes with Indoles
A1 Cooper, Lisa
A1 Alonso Gómez, José Miguel
A1 Eagling, Louise
A1 Newson, Helen
A1 Herath, Sachini
A1 Thomson, Christopher
A1 Lister, Andrew
A1 Howsham, Catherine
A1 Cox, Brian
A1 Muñoz, María Paz
AB 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.
PB Wiley
SN 0947-6539
YR 2018
FD 2018
LK https://hdl.handle.net/20.500.14352/92592
UL https://hdl.handle.net/20.500.14352/92592
LA eng
NO 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.
NO University of East Anglia (Reino Unido)
NO Engineering & Physical Sciences Research Council (Reino Unido)
NO The Leverhulme Trust (Reino Unido)
DS Docta Complutense
RD 31 ago 2024