A broad‐spectrum synthesis of Tetravinylethylenes
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Colleges, School and Institutes
The first general synthesis of compounds of the tetravinylethylene (TVE) family is reported. Ramirez‐type dibromo‐olefination of readily accessible penta‐1,4‐dien‐3‐ones generates 3,3‐dibromodendralenes, which undergo twofold Negishi, Suzuki‐Miyaura or Mizoroki‐Heck reactions with a wide variety of olefinic coupling partners. This route delivers a broad range of unsymmetrically–substituted tetravinylethylenes with up to three different alkenyl substituents attached to the central C=C bond. The extensive scope of the approach is demonstrated by the preparation of the first higher order oligo‐alkenic through‐conjugated/cross‐conjugated hybrid compounds. An unsymmetrically‐substituted TVE is shown to undergo a domino electrocyclization‐cycloaddition with high site‐selectivity and diastereoselectivity, thereby demonstrating the substantial synthetic potential of substituted TVEs for controlled, rapid structural complexity generation.
|Number of pages||5|
|Journal||Chemistry: A European Journal|
|Early online date||6 Feb 2019|
|Publication status||Published - 15 Mar 2019|