54624-35-0

Upstream product

• 162707-95-1 3-phenyl-2,2-bis<2-propen-1-yl>thiirane 
• 556-56-9 allyl iodid 
• 7436-90-0 2,2-dibromostyrene 
• 106-95-6 allyl bromide 
• 2882-19-1 ethyl 2-phenyl-2-bromoacetate 
• 162707-85-9 2-(benzothiazol-2-thio)-1-phenyl-2-(2-propen-1-yl)-4-penten-1-one 
• 13944-95-1 2-(phenacylsulfanyl)-1,3-benzothiazole 
• 407617-08-7 1,1,1-tribromo-2-phenyl-2-(trimethylsiloxy)ethane 

Relevant academic research and scientific papers

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.

Applications of allylsamarium bromide as a grignard reagent and a singleelectron transfer reagent in the one-pot synthesis of dienes and trienes

The utility of allylsamarium bromide, both as a nucleophilic reagent and a single-electron transfer (SET) reagent in the reaction of α-halo, γ-halo-αβ-unsaturated ketones and esters with allylsamarium bromide is reported for the first time in this paper. From a synthetic point of view, a general, efficient and experimentally simple one-pot method for the preparation of 1,4-dienes and trienes is developed. A possible mechanism of the transformation is proposed.

Highly efficient allyl cross-coupling reactions of allylindiums with organic electrophiles

This paper describes highly efficient allyl cross-coupling reactions of allylindiums with organic electrophiles such as aryl and vinyl triflates, vinyl halides, dibromoolefin, and alkynyl iodide. The reactions were carried out using 4 mol % Pd(PPh3)4 in the presence of 3 equiv of LiCl in DMF at 100 °C under a nitrogen atmosphere. Allylindium, generated from the reaction of 1 equiv of indium with 1.5 equiv of allyl halide, gave the best result as a coupling partner. The present method is mild and simple to apply, and it produces a diverse range of allylic compounds in good to excellent yields.

Synthesis of trisubstituted and tetrasubstituted alkenes via a manganate-induced migration-elimination process

Preparation of alkenes via a manganate-induced alkylation-elimination sequence was investigated. The reaction of 2-alkoxy-1,1-dibromoalkanes with trialkylmanganates afforded disubstituted or trisubstituted alkenes. Treatment of 2-alkoxy-1,1,1-tribromoalkanes with trialkylmanganates provided trisubstituted or tetrasubstituted alkenes through bromine-metal exchange, transfer of two alkyl groups from manganese to carbon, and successive elimination of metal and the β-alkoxy moieties.

Palladium-catalysed Synthesis of α-Diallylated Ketosulphides of Benzothiazole and their Transformation into Diallyl Thiiranes and Trienes

α-Ketosulphides of benzothiazole 1 react with allylic carbonates in the presence of palladium acetate in dichloromethane under mild conditions affording α,α-diallylated ketosulphides 2 in high yields.Reduction of 2 with sodium borohydride in isopropanol gives episulphides which in turn can be transformed almost quantitatively into trienes.

Aminium Salts Induced Desulphurization of Allyl and Diallyl Thiiranes. Synthesis of Dienes and Trienes

Catalytic amounts of aminium salts A-B induce the conversion of methylene chloride in solutions of several allyl and diallyl episulphides 1-6 into the corresponding unsaturated derivatives 7-12.The desulphurization process, which occurs through a plausible chain electron-transfer mechanism, rapid and may proceed in a fashion that preserves the stereochemistry of the starting episulphide.