Please use this identifier to cite or link to this item: http://hdl.handle.net/2440/118364
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Type: Journal article
Title: A broad-spectrum synthesis of tetravinylethylenes
Author: Horvath, K.
Newton, C.
Roper, K.
Ward, J.
Sherburn, M.
Citation: Chemistry - A European Journal, 2019; 25(16):4072-4076
Publisher: Wiley
Issue Date: 2019
ISSN: 0947-6539
1521-3765
Statement of
Responsibility: 
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-dibromo[3]dendralenes, 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
RMID: 0030110445
DOI: 10.1002/chem.201900550
Appears in Collections:Chemistry publications

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