Projects per year
Abstract
By exploring lithium‐bromide exchange reactivity of aromatic Schiff’s bases with tert‐butyllithium (tBuLi) we have revealed unprecedented competitive intermolecular and intramolecular cascade annulation pathways leading to valuable compounds such as iso‐indolinones and N‐substituted anthracene derivatives. A series of reaction parameters were probed including solvent, stoichiometry, sterics and organolithium reagent choice in order to understand the influences limiting such ring closing pathways. In the case of having two viable reactivity options for the organolithium on the imine; namely nucleophilic addition or lithium‐bromide exchange, a surprising competitive nature was observed where nucleophilic addition dominated, even under cryogenic conditions. Considering the most commonly used solvents for lithium‐bromide exchange, tetrahydrofuran (THF) and diethyl ether (Et2O), contrasting reactivity outcomes were revealed with nucleophilic addition promoted in THF, while Et2O yielded almost double the conversion of cyclic products than in THF.
Original language | English |
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Pages (from-to) | 11876-11882 |
Number of pages | 7 |
Journal | Chemistry - A European Journal |
Volume | 25 |
Issue number | 51 |
DOIs | |
Publication status | Published - 2019 |
Projects
- 1 Finished
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Expanding the Organometallic Toolbox for Constructing Novel Heterocycles
Andrews, P., Blair, V. & Bull, S.
Australian Research Council (ARC), Monash University, University of Bath
1/01/17 → 31/05/20
Project: Research
Equipment
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Australian Synchrotron
Office of the Vice-Provost (Research and Research Infrastructure)Facility/equipment: Facility