Short-Step Synthesis of a Resveratrol Derivative from Commercially Available 1,3-Dimethoxybenzene and 4-Vinylanisole

Abstract

An efficient synthesis of tri-O-methylated resveratrol is presented using an advanced Heck reaction promoted by Pd(dba) 2 in the presence of P(t-Bu) 3 .

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

“…Therefore, Pd‐catalyzed cross‐coupling reactions are very effective alternatives due to their synthetic versatility and efficiency 17. Suzuki reactions between β‐halostyrenes and arylboronic acids,18–20 decarbonylative Heck reactions between resorcylic acid chlorides and styrenes,21, 22 and Heck reactions between aryl halides and styrene derivatives regioselectively furnish the trans ‐stilbene coupling products in one step;23–32 however, in all of these cases, a styrene derivative substrate is required. Although some styrene derivatives are commercially available, most need to be prepared by elimination reactions, partial alkyne reductions, carbonyl olefination methods or, more recently, via Pd‐catalyzed cross‐coupling reactions 33.…”

Synthesis of legioliulin, a fluorescent isocoumarin compound, isolated from Legionella dumoffii using cyclic acylpalladation and Heck reaction

“…was effective ligand to form stilbene framework. 12 Fu reported that the effect of P(t-Bu)3. 13 According to his report, the effect of P(t-Bu)3 is electron donating as well as accelerating reductive elimination.…”