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https://hdl.handle.net/2440/118364
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Type: | Journal article |
Title: | A broad-spectrum synthesis of tetravinylethylenes |
Author: | Horvath, K.L. Newton, C.G. Roper, K.A. Ward, J.S. Sherburn, M.S. |
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 |
DOI: | 10.1002/chem.201900550 |
Published version: | http://dx.doi.org/10.1002/chem.201900550 |
Appears in Collections: | Aurora harvest 8 Chemistry publications |
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