Volume 25, Issue 4 pp. 289-293

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The synthesis of non-symmetrical stilbene analogs of trans-resveratrol using the same Pd catalyst in a sequential double-Heck arylation of ethylene

Sabrina M. Nobre,

Sabrina M. Nobre

Instituto de Química, UFRGS, Av. Bento Gonçalves, 9500 Porto Alegre 91501-970, CP 15003, RS, Brazil

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Mauro N. Muniz,

Mauro N. Muniz

Instituto de Química, UFRGS, Av. Bento Gonçalves, 9500 Porto Alegre 91501-970, CP 15003, RS, Brazil

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Marcus Seferin,

Marcus Seferin

Faculdade de Química—PUCRS, Av. Ipiranga, 6681, Porto Alegre, 90619-900, RS, Brazil

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Wagner M. da Silva,

Wagner M. da Silva

Faculdade de Química—PUCRS, Av. Ipiranga, 6681, Porto Alegre, 90619-900, RS, Brazil

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Adriano L. Monteiro,

Corresponding Author

Adriano L. Monteiro

[email protected]

Instituto de Química, UFRGS, Av. Bento Gonçalves, 9500 Porto Alegre 91501-970, CP 15003, RS, Brazil

Instituto de Química, UFRGS, Av. Bento Gonçalves, 9500 Porto Alegre 91501-970, CP 15003, RS, Brazil.Search for more papers by this author

Sabrina M. Nobre,

Sabrina M. Nobre

Instituto de Química, UFRGS, Av. Bento Gonçalves, 9500 Porto Alegre 91501-970, CP 15003, RS, Brazil

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Mauro N. Muniz,

Mauro N. Muniz

Instituto de Química, UFRGS, Av. Bento Gonçalves, 9500 Porto Alegre 91501-970, CP 15003, RS, Brazil

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Marcus Seferin,

Marcus Seferin

Faculdade de Química—PUCRS, Av. Ipiranga, 6681, Porto Alegre, 90619-900, RS, Brazil

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Wagner M. da Silva,

Wagner M. da Silva

Faculdade de Química—PUCRS, Av. Ipiranga, 6681, Porto Alegre, 90619-900, RS, Brazil

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Adriano L. Monteiro,

Corresponding Author

Adriano L. Monteiro

[email protected]

Instituto de Química, UFRGS, Av. Bento Gonçalves, 9500 Porto Alegre 91501-970, CP 15003, RS, Brazil

Instituto de Química, UFRGS, Av. Bento Gonçalves, 9500 Porto Alegre 91501-970, CP 15003, RS, Brazil.Search for more papers by this author

First published: 06 January 2011

https://doi.org/10.1002/aoc.1756

Citations: 12

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Abstract

We have developed a sequential and selective Pd-catalyzed double-Heck arylation of ethylene that results in non-symmetrical nitro-stilbene analogs of trans-resveratrol at excellent yields. A catalytic system consisting of Pd(OAc)₂ and P(o-tolyl)₃ permitted us to carry out the two consecutive Heck arylations without losing activity from the first to the second Heck reaction. After the first Heck arylation of ethylene, no isolation or additional catalyst loading is required for the second Heck arylation reaction. This protocol was applied to the synthesis of methylated trans-resveratrol, which was obtained at a 65% overall yield. Copyright © 2011 John Wiley & Sons, Ltd.

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Volume25, Issue4

April 2011

Pages 289-293

The synthesis of non-symmetrical stilbene analogs of trans-resveratrol using the same Pd catalyst in a sequential double-Heck arylation of ethylene

Abstract

References

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References

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The synthesis of non-symmetrical stilbene analogs of trans-resveratrol using the same Pd catalyst in a sequential double-Heck arylation of ethylene

Abstract

References

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