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Develop a versatile synthetic route to hexadienes using palladium-catalyzed decarboxylative sp3–sp3 coupling coupled with a Cope rearrangement.

July 4, 2006Angewandte Chemie

A Versatile Hexadiene Synthesis by Decarboxylative sp3–sp3 Coupling/Cope Rearrangement

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Develop a versatile synthetic route to hexadienes using palladium-catalyzed decarboxylative sp3–sp3 coupling coupled with a Cope rearrangement.
Subjected esters containing two allyl groups to palladium-catalyzed decarboxylative coupling.
Regulated reaction temperatures to steer product formation between kinetic α-allylation and subsequent thermal Cope rearrangement pathways.
Palladium-catalyzed decarboxylative coupling yields kinetic allylation products at the α-position relative to electron-withdrawing groups.
Tandem coupling followed by Cope rearrangement affords access to γ-coupling products.
Target regioisomers can be selectively accessed simply by adjusting the reaction temperature.

Implication

Chemical synthesis study demonstrates temperature-controlled regioisomer selection during tandem allylation, highlighting a tunable pathway to functionalized hexadienes.

Abstract

Freie Wahl: Die palladiumkatalysierte decarboxylierende Kupplung von Estern mit zwei Allylgruppen führt zur kinetischen Allylierung in α-Position zu elektronenziehenden Gruppen. Die Tandem-Allylierung/Cope-Umlagerung eröffnet den Zugang zu γ-Kupplungsprodukten (siehe Schema). Somit kann man das gewünschte Regioisomer einfach über die Reaktionstemperatur auswählen.

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Cite This Study

Waetzig et al. (2006) studied this question.

synapsesocial.com/papers/6a9e4c0b6e3e9028e6be6176 https://doi.org/10.1002/ange.200600721

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Implication

Chemical synthesis study demonstrates temperature-controlled regioisomer selection during tandem allylation, highlighting a tunable pathway to functionalized hexadienes.

A Versatile Hexadiene Synthesis by Decarboxylative sp3–sp3 Coupling/Cope Rearrangement

Key Points

Implication

Abstract

Discussion

Cite This Study

A Versatile Hexadiene Synthesis by Decarboxylative sp3–sp3 Coupling/Cope Rearrangement

Key Points

Implication

Abstract

Discussion

Cite This Study

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