Nickel-catalysed synthesis of multisubstituted pyrroles by anti-carbometallative cyclisations

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Gillbard, Simone Marie (2019) Nickel-catalysed synthesis of multisubstituted pyrroles by anti-carbometallative cyclisations. MSc(Res) thesis, University of Nottingham.

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Abstract

Herein is presented the first example of nickel-catalysed cyclisation of Ntosylalkynamides with arylboronic acids to give 2,3,4-trisubstituted pyrroles. The reaction is initiated by alkyne arylnickelation and proceeds via an essential E/Z isomerisation step which allows for cyclisation. An investigation of the scope of the reaction and the boronic acid gave rise to 25 examples in 46-99% yield.

Further, the described method was successfully applied to the synthesis of precursors to BODIPY derivatives and it was attempted to apply the method to the synthesis of the group of marine alkaloids, lamellarins.

Item Type: Thesis (University of Nottingham only) (MSc(Res))
Supervisors: Lam, Hon Wai
Keywords: pyrroles; lamellarins; nickel-catalysed synthesis
Subjects: Q Science > QD Chemistry > QD241 Organic chemistry
Faculties/Schools: UK Campuses > Faculty of Science > School of Chemistry
Item ID: 56140
Depositing User: Gillbard, Simone
Date Deposited: 17 Sep 2019 12:28
Last Modified: 17 Jul 2021 04:30
URI: https://eprints.nottingham.ac.uk/id/eprint/56140

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