Lithium-Bromide Exchange versus Nucleophilic Addition of Schiff's base: Unprecedented Tandem Cyclisation Pathways.

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ID: 100181
2019
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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 that limit such ring-closing pathways. With 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 (Et O), contrasting reactivity outcomes were revealed with nucleophilic addition promoted in THF, while Et O yielded almost double the conversion of cyclic products than in THF.
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orr2019lithiumbromidechemistry Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Orr, Samantha A;Border, Emily C;Andrews, Philip C;Blair, Victoria L;
Journal Chemistry (Weinheim an der Bergstrasse, Germany)
Year 2019
DOI
10.1002/chem.201902140
URL
Keywords
nucleophilic addition cyclisation imines iso-indolinones lithium-bromide exchange

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