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|Title:||A broad-spectrum synthesis of tetravinylethylenes|
|Citation:||Chemistry - A European Journal, 2019; 25(16):4072-4076|
|Kelsey L. Horvath, Dr. Christopher G. Newton, Dr. Kimberley A. Roper, Dr. Jas S. Ward, Michael S. Sherburn|
|Abstract:||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.|
|Keywords:||Cross-coupling; cycloaddition; electrocyclic reactions; hydrocarbons; polyenes|
|Rights:||© 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim|
|Appears in Collections:||Chemistry publications|
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