78237-66-8Relevant academic research and scientific papers
Ligand-controlled palladium-catalyzed regiodivergent suzuki-miyaura cross-coupling of allylboronates and aryl halides
Yang, Yang,Buchwald, Stephen L.
supporting information, p. 10642 - 10645 (2013/08/23)
An orthogonal set of catalyst systems has been developed for the Suzuki-Miyaura coupling of 3,3-disubstituted and 3-monosubstituted allylboronates with (hetero)aryl halides. These methods allow for the highly selective preparation of either the α- or the
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.
Synthesis and Dediazoniation of 2-Butyl- and 2,5-Dibutylbenzenediazonium Ions
Sikkar, Rein,Martinson, Per
, p. 551 - 558 (2007/10/02)
2-Butylbenzenediazonium ion (1a) and 2,5-dibutylbenzenediazonium ion (1b) have been thermally decomposed in aqueous acid solution.In addition to the major product, the corresponding phenol, 5- and 6-membered ring products are formed (in a ratio of ca. 7:1) as well as products of elimination and substitution in the o-butyl group.The formation of the non-phenolic products is explained in terms of competing reactions of the initially formed aryl cations: cyclization by electrophilic atttack on the o-butyl group and 1,5-hydride ion transfer from the o-butyl group with concomitant elimination or reaction with the medium.Decompositions of 1a in the presence of copper(I) oxide, believed to generate aryl radicals, does not yield any measurable quantities of cyclized products, however.
