1044231-36-8Relevant articles and documents
Microwave-assisted, ligand-free, direct C-H arylation of thiophenes in biomass-derived γ-valerolactone
Tabasso, Silvia,Calcio Gaudino, Emanuela,Rinaldi, Laura,Ledoux, Audrey,Larini, Paolo,Cravotto, Giancarlo
, p. 9210 - 9215 (2017)
The Pd-catalyzed C-H arylation of heterocycles with aryl halides is a straightforward and more environmentally-friendly route to the synthesis of well-defined, pi-conjugated polymers for challenging applications in electronic devices. Although this type of transformation is more atom efficient than cross-couplings, it still poses environmental issues in the form of reaction media and the use of phosphine ligands. A procedure for the C-H arylation of thiophenes, with a substantially improved environmental impact, and a promising application of this protocol to the synthesis of regioregular polythiophenes are reported in this work. γ-Valerolactone (GVL), a non-toxic biomass-derived solvent, has been used in this phosphine-free microwave-assisted process and replaces commonly used dipolar aprotic media. Activated aryl bromides gave arylthiophenes in good yields, while iodides were used and pivalic acid was added when electron-withdrawing groups were present. The reaction was also extended to C-H (hetero)arylation polycondensation and a high molecular weight poly(3-hexyl)thiophene was obtained, using low Pd loading, in high yields and good regioregularity in short reaction times. Computational studies have shed light on GVL's role as a ligand in the catalytic system.
Palladium Complexes with Tetrahydropyrimidin-2-ylidene Ligands: Catalytic Activity for the Direct Arylation of Furan, Thiophene, and Thiazole Derivatives
Karaca, Emine ?zge,Gürbüz, Nevin,?zdemir, Ismail,Doucet, Henri,?ahin, Onur,Büyükgüng?r, Orhan,?etinkaya, Bekir
, p. 2487 - 2493 (2015/06/25)
The synthesis and characterization of novel 1,3-benzyl-3,4,5,6-tetrahydropyrimidin-2-ylidene-based N-heterocyclic carbene palladium(II) complexes (1a-d) were described. The crystal structure of trans-dichlorobis[1,3-bis(4-methylbenzyl)-3,4,5,6-tetrahydrop
Modular functionalized polyphosphines for supported materials: Previously unobserved 31P-NMR through-space ABCD spin systems and heterogeneous palladium-catalysed C-C and C-H arylation
Beauperin, Matthieu,Smaliy, Radomyr,Cattey, Helene,Meunier, Philippe,Ou, Jun,Toy, Patrick H.,Hierso, Jean-Cyrille
supporting information, p. 9505 - 9508 (2014/08/18)
The modular design of polyphosphines, diversely functionalized for facile immobilization on virtually any kind of support, is reported. Previously unobserved ABCD 31P NMR spin-spin systems evidence the control exercised on the polyphosphines co
