73318-85-1

Upstream product

• 36934-19-7 2,3,3-trimethyl-4-penten-2-ol 
• 99-91-2 para-chloroacetophenone 
• 99-90-1 para-bromoacetophenone 
• 141550-13-2 4,4,5,5-tetramethyl-2-(3-methylbut-2-enyl)-1,3,2-dioxaborolane 
• 13329-40-3 4-Iodoacetophenone 
• 870-63-3 prenyl bromide 
• 114067-34-4 (3-methyl-2-butenyl)trifluorosilane 

Downstream Products

• 73318-86-2 1-(p-prenylphenyl)-ethanol 

Relevant academic research and scientific papers

Regioselective cross-coupling of allylboronic acid pinacol ester derivatives with aryl halides via Pd-PEPPSI-IPent

The cross-coupling reactions of allylboronic acid pinacol ester derivatives with aryl and heteroaryl halides occurred with high selectivity (>97%) at the α-carbon of the allylboron reagent in the presence of Pd-PEPPSI-IPent precatalyst and 5 M KOH in refluxing THF. In the case of trisubstituted allylboronates with different substituents on the olefin, minor olefin geometry isomerization was observed (E/Z & 80/20).

Palladium-catalyzed allyl cross-coupling reactions with in situ generated organoindium reagents

Inter- and intramolecular palladium-catalyzed allyl cross-coupling reactions, using allylindium generated in situ from allyl halides and indium, is demonstrated. Allylindium compounds may be effective nucleophilic coupling partners in palladium-catalyzed cross-coupling reactions. A variety of allyl halides, such as allyl iodide, allyl bromide, crotyl bromide, prenyl bromide, geranyl bromide, and 3-bromocyclohexene afforded the allylic cross-coupling products in good to excellent yields. Stereochemistry of the double bond is retained in the allylic cross-coupling reactions. Electrophilic cross-coupling partners, such as aryl and vinyl halides, dibromoolefin, alkynyl iodide, and aryl and vinyl triflates participate in these reactions. The presence of various substituents, such as n-butyl, ketal, acetyl, ethoxycarbonyl, nitrile, N-phenylamido, nitro, and chloride groups on the aromatic ring of electrophilic coupling partners showed little effect on the efficiency of the reactions. The present conditions work equally well for not only intermolecular but also intramolecular palladium-catalyzed cross-coupling reactions. These methods provide an efficient synthetic method for the introduction of an allyl group, which can be easily further functionalized to afford an sp2- and sp-hybridized carbon. The present method complements existing synthetic methods as a result of advantageous features such as easy preparation and handling, thermal stability, high reactivity and selectivity, operational simplicity, and low toxicity of allylindium reagents.

Synthesis of prenylarenes and related (multisubstituted allyl)arenes from aryl halides and homoallyl alcohols via palladium-catalyzed retro-allylation

The reactions of aryl halides with 2,3,3-trimethyl-4-penten-2-ol in the presence of a palladium catalyst result in prenyl transfer from the alcohol to aryl halides via retro-allylation, yielding prenylarenes. Other multisubstituted allyl groups such as th

Palladium-catalyzed cross-coupling reactions of in situ generated allylindium reagents with aryl halides

(equation presented) X = Br, I In situ generated allylindium reagents from the reaction of 1 equiv of indium with 1.5 equiv of allyl halides could be effective cross-coupling partners in palladium-catalyzed cross-coupling reactions to aryl halides. The best results were obtained with 2% Pd2dba3CHCl3 and 16% Ph3P in the presence of 3 equiv of LiCl in DMF at 100 °C.

α-Selective cross-coupling reaction of allyltrifluorosilanes: Remarkable ligand effect on the regiochemistry

The cross-coupling reaction of allyltrifluorosilanes with aryl halides or aryl triflates promoted by a fluoride salt takes place at the α-carbon of the allyltrifluorosilanes in the presence of a catalytic amount of PdCl2[Ph2P(CH

2-(p-Prenylphenyl)propionic acid

2-(p-prenylphenyl)propionic acid and pharmaceutically acceptable salts thereof are disclosed. They exhibit anti-inflammatory and analgesic activity with low gastrointestinal action.