842124-16-7Relevant articles and documents
Transition-metal-free arylations via photogenerated triplet 4-alkyl- and 4-trimethylsilylphenyl cations
Qrareya, Hisham,Raviola, Carlotta,Protti, Stefano,Fagnoni, Maurizio,Albini, Angelo
, p. 6016 - 6024 (2013/07/26)
The irradiation in protic solvents of 4-chloroalkylbenzenes and 4-chlorophenyltrimethylsilane caused the heterolytic cleavage of aryl-chlorine bonds to give the corresponding triplet phenyl cations. These were exploited for transition-metal-free arylation reactions under mild conditions to give allylbenzenes, γ-benzyl lactones, 3-arylacetals (ketals), and biaryls in moderate to good yields. The path followed was supported by DFT calculations at the UB3LYP/6-311+G(2d,p) level.
Palladium-catalyzed allyl cross-coupling reactions with in situ generated organoindium reagents
Lee, Kooyeon,Kim, Hyunseok,Mo, Juntae,Lee, Phil Ho
scheme or table, p. 2147 - 2157 (2011/10/31)
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.
Palladium-indium-indium(III) chloride-mediated allyl cross-coupling reactions using allyl acetates
Lee, Phil Ho,Seomoon, Dong,Lee, Kooyeon,Kim, Sundae,Kim, Hyunseok,Kim, Hyun,Shim, Eunkyong,Lee, Miae,Lee, Seokju,Kim, Misook,Sridhar, Madabhushi
, p. 1641 - 1645 (2007/10/03)
Allylindiums in situ generated by reductive transmetalation of π-allylpalladium(II) complexes, obtained from allyl acetates and palladium(0) catalyst, with indium and indium(III) chloride are effective nucleophilic cross-coupling partners in Pd-catalyzed allyl cross-coupling reactions with a variety of electrophilic cross-coupling partners.