3815-20-1Relevant articles and documents
Arylzinc Halides by Silver Catalyzed Zinc Insertion into Aryl Iodides
Casotti, Gianluca,Iuliano, Anna,Carpita, Adriano
, p. 1021 - 1026 (2019/01/04)
A catalytic amount of silver acetate efficiently promotes direct insertion of zinc metal into aryl iodides, having different structure, in ethereal solvent. Electron-rich substrates also rapidly undergo oxidative metalation. The arylzinc iodides formed give Negishi coupling products under mild reaction conditions to obtain biaryls in high yields. Sensitive functional groups like aldehydes and primary amides are well-tolerated.
One-Pot Preparation of Aromatic Amides, 4-Arylthiazoles, and 4-Arylimidazoles from Arenes
Yamamoto, Takahiro,Togo, Hideo
, p. 4187 - 4196 (2018/08/21)
Simple treatment of arenes with α-bromoacetyl chloride and AlCl3, followed by the reaction with molecular iodine and aq. NH3, thioamides, or amidines gave the corresponding primary aromatic amides, 4-arylthiazoles, or 4-arylimidazoles in good yields, respectively. Aryl α-bromomethyl ketones are the key intermediates in those reactions. Primary aromatic amides were formed from arenes through the reaction of aryl α-bromomethyl ketones with molecular iodine and aq. NH3, and 4-arylthiazoles and 4-arylimidazoles were formed from arenes through the reactions of aryl α-bromomethyl ketones with thioamides and amidines, respectively, in one pot under transition-metal-free conditions.
Dithioester-enabled chemodivergent synthesis of acids, amides and isothiazoles via C[sbnd]C bond cleavage and C[sbnd]O/C[sbnd]N/C[sbnd]S bond formations under metal- and catalyst-free conditions
Soni, Sonam,Koley, Suvajit,Singh, Maya Shankar
supporting information, p. 2512 - 2516 (2017/05/31)
An operationally simple and user-friendly process to access privileged scaffolds such as acids, amides and isothiazoles has been devised employing β-ketodithioesters for the first time. Remarkably, the new protocol involves combination of C[sbnd]C bond cl
Room-temperature photoinduced direct C-H-arylation via base-promoted homolytic aromatic substitution
Budén, María E.,Guastavino, Javier F.,Rossi, Roberto A.
supporting information, p. 1174 - 1177 (2013/04/24)
Conceptually different approach toward biaryl syntheses by photoinduced direct C-H arylation of benzene and thiophene in the presence of t-BuOK is reported. The reaction proceeds through photo- and base-promoted homolytic aromatic substitution. The o-, m- and p- substituted ArI, as well as the electron-donating and electron-withdrawing nature of the substituents were found be good to excellent substrates. Heteroaryl, ArBr, ArCl and double C-H arylation were successfully achieved.
PVP-stabilized palladium nanoparticles electrochemically obtained as effective catalysts in aqueous medium Suzuki-Miyaura reaction
Uberman, Paula M.,Martin, Sandra E.,Perez, Luis A.,Lacconi, Gabriela I.
, p. 245 - 253,9 (2020/07/31)
In this paper the synthesis of stable palladium nanoparticles (PdNPs) by electrochemical methods at room temperature is reported. Direct electroreduction of H2PdCl4 aqueous solution in the presence of poly-(N-vinyl-2-pirrolydone) (PVP) onto platinum electrodes was performed by the application of a constant current density pulse. By simultaneous stirring of the electrolyte, the NPs formed on the electrode surface were stabilized with PVP in the solution. The resulting PdNPs were characterized by transmission electron microscopy and the total content of palladium was analytically determined by atomic absorption measurements. The average size of the NPs (in the range of 10-22 nm) was tuned by changing the current density applied. The PdNPs prepared by this methodology exhibited highly efficient catalytic activity on Suzuki-Miyaura coupling reaction in aqueous medium. Particularly high turnover numbers (TON up to 104-105) were achieved by these PVP-stabilized PdNPs with aryl iodides and bromides.
Benzamide synthesis by direct electrophilic aromatic substitution with cyanoguanidine
Naredla, Rajasekhar Reddy,Klumpp, Douglas A.
experimental part, p. 4779 - 4781 (2012/09/07)
Cyanoguanidine is an inexpensive commodity chemical and it is found to be a useful reagent for the direct Friedel-Crafts carboxamidation of arenes. The reaction works best in an excess of Bronsted superacid, an observation suggesting the involvement of a superelectrophilic intermediate. Theoretical calculations indicate that the most stable diprotonated species involves protonation at the guanidine and cyano nitrogen atoms.
Palladium-containing perovskites: Recoverable and reuseable catalysts for Suzuki couplings
Smith, Martin D.,Stepan, Antonia F.,Ramarao, Chandrashekar,Brennan, Paul E.,Ley, Steven V.
, p. 2652 - 2653 (2007/10/03)
Palladium-containing perovskites (LaFe0.57 Co0.38Pd0.05O3) have been exploited as recoverable and reuseable catalysts in Suzuki coupling reactions; residual levels of Pd after removal of the catalyst by filtration are low (2 ppm) despite evidence that the reaction is occurring via a homogeneous process.
