Please use this identifier to cite or link to this item:
https://hdl.handle.net/2440/118364
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dc.contributor.author | Horvath, K.L. | - |
dc.contributor.author | Newton, C.G. | - |
dc.contributor.author | Roper, K.A. | - |
dc.contributor.author | Ward, J.S. | - |
dc.contributor.author | Sherburn, M.S. | - |
dc.date.issued | 2019 | - |
dc.identifier.citation | Chemistry: A European Journal, 2019; 25(16):4072-4076 | - |
dc.identifier.issn | 0947-6539 | - |
dc.identifier.issn | 1521-3765 | - |
dc.identifier.uri | http://hdl.handle.net/2440/118364 | - |
dc.description.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. | - |
dc.description.statementofresponsibility | Kelsey L. Horvath, Dr. Christopher G. Newton, Dr. Kimberley A. Roper, Dr. Jas S. Ward, Michael S. Sherburn | - |
dc.language.iso | en | - |
dc.publisher | Wiley | - |
dc.rights | © 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim | - |
dc.source.uri | http://dx.doi.org/10.1002/chem.201900550 | - |
dc.subject | Cross-coupling | - |
dc.subject | cycloaddition | - |
dc.subject | electrocyclic reactions | - |
dc.subject | hydrocarbons | - |
dc.subject | polyenes | - |
dc.title | A broad-spectrum synthesis of tetravinylethylenes | - |
dc.type | Journal article | - |
dc.identifier.doi | 10.1002/chem.201900550 | - |
pubs.publication-status | Published | - |
dc.identifier.orcid | Newton, C.G. [0000-0002-8962-5917] | - |
Appears in Collections: | Aurora harvest 8 Chemistry publications |
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