580-82-5Relevant articles and documents
Palladium-mediated radical homocoupling reactions: A surface catalytic insight
Favier, Isabelle,Toro, Marie-Lou,Lecante, Pierre,Pla, Daniel,Gómez, Montserrat
, p. 4766 - 4773 (2018/09/29)
In this contribution, we report a palladium nanoparticle-promoted reductive homocoupling of haloarenes that proceeds efficiently to produce corresponding bis-aryls in moderate to excellent yields using relatively low catalyst loading (1 mol%), and exhibits broad functional group tolerance. This work sheds light on how the surface state of Pd(0) nanoparticles plays a crucial role in the reactivity of catalytic systems. Notably, the appropriate choice of palladium salts for the preparation of the preformed nanocatalysts was a key parameter having a major impact on the catalytic activity; thus, the effect of halide anions on the reactivity of the as-prepared palladium nanoparticles could be assessed, with iodide anions being capable of inhibiting the corresponding homocoupling reaction. The homocoupling reaction mechanism has been further studied by means of radical trap and electron paramagnetic resonance (EPR) experiments, revealing that the reaction proceeds via radical intermediates. Taking into account these data, a plausible reaction mechanism based on single-electron transfer processes on the palladium nanoparticle surface is discussed.
Iron-catalyzed homocoupling of aryl halides and derivatives in the presence of alkyllithiums
Toummini, Dounia,Ouazzani, Fouad,Taillefer, Marc
supporting information, p. 4690 - 4693 (2013/10/08)
Direct synthesis of biaryl derivatives from aryl halides takes place under very mild temperature conditions by using a ligand-free iron catalytic system. The procedure, which proceeds via an in situ quantitative aryl halide exchange with alkyllithiums, allows for excellent control of the reactivity and is in line with the sustainable development. The method is also applicable to styryl and benzyl halides and to phenylacetylene.
Synthesis of functionalized 2-arylthiophenes with triarylbismuths as atom-efficient multicoupling organometallic nucleophiles under palladium catalysis
Rao, Maddali L. N.,Banerjee, Debasis,Dhanorkar, Ritesh J.
supporting information; experimental part, p. 1324 - 1330 (2011/07/07)
Atom-efficient cross-coupling reactions of functionalized 2-bromo- and 2-iodothiophenes have been demonstrated using triarylbismuths as atom-efficient multicoupling organometallic nucleophiles under palladium-catalyzed conditions. These couplings with various functionalized triarylbismuths proceeded smoothly to afford the corresponding functionalized 2-arylthiophenes in high yields. Georg Thieme Verlag Stuttgart · New York.