118959-33-4Relevant articles and documents
Copper-mediated selective cyanation of indoles and 2-phenylpyridines with ammonium iodide and DMF
Kim, Jinho,Kim, Hyunwoo,Chang, Sukbok
, p. 3924 - 3927 (2012)
Copper-mediated regioselective cyanation of indoles and 2-phenylpyridines was developed by using ammonium iodide and DMF as the combined source of a cyano unit under Pd-free conditions. Mechanistic studies indicate that the reaction of indoles proceeds through a two-step sequence: electrophilic initial iodination and then cyanation. The cyanation has a broad substrate scope, high functional group tolerance, and excellent regioselectivity.
An insight on the influence of surface Lewis acid sites for regioselective C–H bond C3-cyanation of indole using NH4I and DMF as combined cyanide source over Cu/SBA-15 catalyst
Boosa, Venu,Bilakanti, Vishali,Velisoju, Vijay Kumar,Gutta, Naresh,Inkollu, Sreedhar,Akula, Venugopal
, p. 43 - 51 (2018)
The Cu dispersed on mesoporous SBA-15 has demonstrated the regioselective C–H bond C3-cyanation of indoles by in-situ generation of –CN using DMF and NH4I in presence of O2. Pyridine adsorbed diffuse reflectance infrared spectroscopy (DRIFTS) results revealed that surface Cu2+ species are acting as Lewis acid sites in the in-situ generation of cyano- group for the synthesis of indole nitriles. A direct correlation between Cu metal surface area and the indole nitrile yields are established and the dual role of copper is substantiated by N2O titration and XPS techniques. The 10 wt%Cu/SBA-15 demonstrated superior performance when compared to Pd, Ru supported on SBA-15. The 10 wt%Cu/SBA-15 catalyst showed consistent activity and selectivity after the 4th cycle.
Copper-mediated C3-cyanation of indoles by the combination of amine and ammonium
Liu, Bin,Wang, Jiehui,Zhang, Bo,Sun, Yang,Wang, Lei,Chen, Jianbin,Cheng, Jiang
, p. 2315 - 2317 (2014)
A copper-promoted C3-cyanation of both the free N-H and N-protected indoles by N,N,N′,N′-tetramethyl-ethane-1,2-diamine (TMEDA) and ammonium is achieved. The iminium ion acts as the intermediate in this transformation, which is sequentially electrophilically attacked by indole and H2O followed by hydrolyzation to form the aldehyde. Then the reaction between the aldehyde and ammonium afforded nitriles. The reaction employs O2 as a clean oxidant with good efficiency and functional group tolerance. Thus, it represents a facile and safe procedure leading to 3-cyano indoles. The Royal Society of Chemistry 2014.
Decarbonylative Synthesis of Aryl Nitriles from Aromatic Esters and Organocyanides by a Nickel Catalyst
Iizumi, Keiichiro,Kurosawa, Miki B.,Isshiki, Ryota,Muto, Kei,Yamaguchi, Junichiro
supporting information, p. 1555 - 1559 (2020/11/10)
A decarbonylative cyanation of aromatic esters with aminoacetonitriles in the presence of a nickel catalyst was developed. The key to this reaction was the use of a thiophene-based diphosphine ligand, dcypt, permitting the synthesis of aryl nitrile without the generation of stoichiometric metal- or halogen-containing chemical wastes. A wide range of aromatic esters, including hetarenes and pharmaceutical molecules, can be converted into aryl nitriles.
Direct C-2 Carboxylation of 3-Substituted Indoles Using a Combined Br?nsted Base Consisting of LiO-tBu/CsF/18-crown-6
Shigeno, Masanori,Tohara, Itsuki,Nozawa-Kumada, Kanako,Kondo, Yoshinori
supporting information, p. 1987 - 1991 (2020/04/09)
Herein, we report that a combination of LiO-tBu, CsF, and 18-crown-6 can be used to carry out the carboxylation of indole derivatives at the C-2 position under an ambient CO2 atmosphere. Substrates bearing an electrophilic substituent (i.e., cyano, formyl, benzoyl, phenylsulfonyl, phenylsulfinyl, and chloride) at the C-3 position are smoothly converted into their corresponding carboxylated products with high functional group compatibility.
