Facile synthesis of symmetrical 3,3-diarylacrylates by a Heck-Matsuda reaction : an expedient route to biologically active indanones.
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Date
2011
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Abstract
A simple and straightforward synthesis of symmetrical 3,3-diarylacrylates based on a Heck-Matsuda reaction of arenediazonium salts bearing electron-donating groups with methylacrylates is described. The reaction employs Pd(OAc)2 as catalyst and goes to completion within 1 h affording the corresponding unsaturated diaryl esters in good to high yields. This method permitted the expeditious and efficient synthesis of the anticancer 3-arylindanone 5 in two operative steps in 43% overall yield.
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Keywords
Arenediazonium tetrafluoroborates, Heck-Matsuda, Arylation, Indanones, Palladium
Citation
TAYLOR, J. G.; RIBEIRO, R. da S.; CORREIA, C. R. D. Facile synthesis of symmetrical 3,3-diarylacrylates by a Heck-Matsuda reaction: an expedient route to biologically active indanones. Tetrahedron Letters, v. 52, p. 3861-3864, 2011. Disponível em: <http://www.sciencedirect.com/science/article/pii/S0040403911007763>. Acesso em: 02 fev. 2015.