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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
Author(s) -
Nobre Sabrina M.,
Muniz Mauro N.,
Seferin Marcus,
da Silva Wagner M.,
Monteiro Adriano L.
Publication year - 2011
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.1756
Subject(s) - chemistry , heck reaction , catalysis , ethylene , resveratrol , yield (engineering) , palladium , organic chemistry , medicinal chemistry , combinatorial chemistry , biochemistry , materials science , metallurgy
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.