63297-58-5

Upstream product

• 100-52-7 benzaldehyde 
• 121862-31-5 (Z)-6-Methyl-1-phenyl-4-phenylsulfanyl-hepta-3,5-dien-1-one 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 121862-24-6 3-Methoxy-6-methyl-1-phenyl-4-phenylsulfanyl-hept-5-en-1-one 
• 115205-36-2 1-Methoxy-4-methyl-1-phenylsulfanyl-pent-3-en-2-ol 
• 3350-78-5 3,3-Dimethylacryloyl chloride 
• 142896-16-0 (E)-1-Phenyl-3-(tri-n-butylstannyl)-2-propen-1-one 

Downstream Products

• 70542-39-1 2-Isopropenyl-3-phenyl-2-cyclopenten-1-on 

Relevant academic research and scientific papers

Synthesis of 1,4-Diketones by Palladium-Catalyzed Reductive Coupling of Acid Chlorides with (E)-1,2-Bis(tri-n-butylstannyl)ethene or β-Stannyl Enones

The palladium-catalyzed coupling of acid chlorides with (E)-1,2-bis(tri-n-butylstannyl)ethene or β-stannyl enones gives butane-1,4-diones directly by reduction of the intermediate enedicarbonyl derivative by a palladium hydride derived from n-Bu3SnCl.

Palladium-Catalyzed Reductive Coupling of Acid Chlorides with β-Stannyl Enones: Synthesis of 1,4-Diketones and Mechanistic Aspects

The palladium-catalyzed coupling of acid chlorides with (E)-1,2-bis(tri-n-butylstannyl)ethene or β-stannyl enones gives butane-1,4-diones directly by reduction of the intermediate enedicarbonyl intermediate.The double bond conjugated with a single carbonyl group was not significantly reduced.The generality of the method is illustrated by two syntheses of the 1,4-diketone ipomeanine.By performing the reaction at lower temperatures, α,β-unsaturated 1,4-diketones can also be prepared.The reduction of the intermediate α,β-unsaturated 1,4-diketones probably proceeds by insertion of a palladium hydride, formed in situ by reaction of a Pd(II) complex with Bu3SnCl, followed by hydrolysis of the intermediate palladium enolate.

DIVERGENT SYNTHESIS OF 1,3- AND 1,4-DIKETONES FROM β-METHOXY-γ-PHENYLTHIO KETONES ACCESSIBLE THROUGH NOVEL PHENYLTHIO MIGRATION REACTION

Both 1,3- and 1.4-diketones are obtained from common precursors, β-methoxy-γ-phenylthio ketones.These compounds are derived through the novel phenylthio migration reaction of the aldehyde adducts with methoxy(phenylthio)-methane upon exposure to enol silyl ethers.The compounds thus obtained are converted into 1,3- and 1,4-diketones.