Abstract
The first chemical synthesis of tetravinylallene (3,5-divinylhepta-1,3,4,6-tetraene) is reported. The final, key step of the synthesis involves a palladium-catalyzed, Negishi-type cross-coupling involving 1,5-transposition of a penta-2-en-4-yn-1-ol methanesulfonate. The unprecedented fundamental hydrocarbon is sufficiently stable to be purified by flash chromatography. A similar synthetic pathway grants access to the first substituted tetravinylallenes, which provide insights into the influence of substitution upon stability and reactivity. Tetravinylallenes are shown to break new ground in swift structural complexity creation, with three novel sequences reported.
Original language | English |
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Pages (from-to) | 14573-14577 |
Number of pages | 5 |
Journal | Angewandte Chemie - International Edition |
Volume | 58 |
Issue number | 41 |
DOIs | |
Publication status | Published - 7 Oct 2019 |