The synthesis of non‐symmetrical stilbene analogs of trans‐resveratrol using the same Pd catalyst in a sequential double‐Heck arylation of ethylene |
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| Authors: | Sabrina M Nobre Mauro N Muniz Marcus Seferin Wagner M da Silva Adriano L Monteiro |
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| Institution: | 1. Instituto de Química, UFRGS, Av. Bento Gon?alves, 9500 Porto Alegre 91501‐970, CP 15003, RS, Brazil;2. Faculdade de Química—PUCRS, Av. Ipiranga, 6681, Porto Alegre, 90619‐900, RS, Brazil |
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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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| Keywords: | Heck reaction palladium trans‐resveratrol stilbene |
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