Nickel-catalysed synthesis of multisubstituted pyrroles by anti-carbometallative cyclisations
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 investiga...
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| Format: | Thesis (University of Nottingham only) |
| Language: | English |
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2019
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| Online Access: | https://eprints.nottingham.ac.uk/56140/ |
| _version_ | 1848799277984251904 |
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| author | Gillbard, Simone Marie |
| author_facet | Gillbard, Simone Marie |
| author_sort | Gillbard, Simone Marie |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | 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. |
| first_indexed | 2025-11-14T20:33:07Z |
| format | Thesis (University of Nottingham only) |
| id | nottingham-56140 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T20:33:07Z |
| publishDate | 2019 |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-561402025-02-28T14:24:51Z https://eprints.nottingham.ac.uk/56140/ Nickel-catalysed synthesis of multisubstituted pyrroles by anti-carbometallative cyclisations Gillbard, Simone Marie 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. 2019-07-17 Thesis (University of Nottingham only) NonPeerReviewed application/pdf en arr https://eprints.nottingham.ac.uk/56140/1/SMG%20Thesis%20-%20corrected%20and%20combined.pdf Gillbard, Simone Marie (2019) Nickel-catalysed synthesis of multisubstituted pyrroles by anti-carbometallative cyclisations. MSc(Res) thesis, University of Nottingham. pyrroles; lamellarins; nickel-catalysed synthesis |
| spellingShingle | pyrroles; lamellarins; nickel-catalysed synthesis Gillbard, Simone Marie Nickel-catalysed synthesis of multisubstituted pyrroles by anti-carbometallative cyclisations |
| title | Nickel-catalysed synthesis of multisubstituted pyrroles by anti-carbometallative cyclisations |
| title_full | Nickel-catalysed synthesis of multisubstituted pyrroles by anti-carbometallative cyclisations |
| title_fullStr | Nickel-catalysed synthesis of multisubstituted pyrroles by anti-carbometallative cyclisations |
| title_full_unstemmed | Nickel-catalysed synthesis of multisubstituted pyrroles by anti-carbometallative cyclisations |
| title_short | Nickel-catalysed synthesis of multisubstituted pyrroles by anti-carbometallative cyclisations |
| title_sort | nickel-catalysed synthesis of multisubstituted pyrroles by anti-carbometallative cyclisations |
| topic | pyrroles; lamellarins; nickel-catalysed synthesis |
| url | https://eprints.nottingham.ac.uk/56140/ |