107536-31-2Relevant academic research and scientific papers
Picolinamides as effective ligands for copper-catalysed aryl ether formation: Structure-activity relationships, substrate scope and mechanistic investigations
Sambiagio, Carlo,Munday, Rachel H.,Marsden, Stephen P.,Blacker, A. John,McGowan, Patrick C.
supporting information, p. 17606 - 17615 (2015/02/05)
The use of picolinic acid amide derivatives as an effective family of bidentate ligands for copper-catalysed aryl ether synthesis is reported. A fluorine-substituted ligand gave good results in the synthesis of a wide range of aryl ethers. Even bulky phenols, known to be very challenging substrates, were shown to react with aryl iodides with excellent yields using these ligands. At the end of the reaction, the first examples of end-of-life Cu species were isolated and identified as CuII complexes with several of the anionic ligands tested. A preliminary mechanistic investigation is reported that suggests that the substituents on the ligands might have a crucial role in determining the redox properties of the metal centre and, consequently, its efficacy in the coupling process. An understanding of these effects is important for the development of new efficient and tunable ligands for copper-based chemistry.
CuO nanoparticles catalyzed C-N, C-O, and C-S cross-coupling reactions: Scope and mechanism
Jammi, Suribabu,Sakthivel, Sekarpandi,Rout, Laxmidhar,Mukherjee, Tathagata,Mandai, Santu,Mitra, Raja,Saha, Prasenjit,Punniyamurthy, Tharmalingam
experimental part, p. 1971 - 1976 (2009/07/01)
CuO nanoparticles have been studied for C-N, C-O, and C-S bond formations via cross-coupling reactions of nitrogen, oxygen, and sulfur nucleophiles with aryl halides. Amides, amines, imidazoles, phenols, alcohols and thiols undergo reactions with aryl iodides in the presence of a base such as KOH, Cs 2CO3, and K2CO3 at moderate temperature. The procedure is simple, general, ligand-free, and efficient to afford the cross-coupled products in high yield.
Highly Efficient C-O Cross-Coupling Reactions with Unactivated Halides by Ligandless, Heterogeneous Raney Ni-Al Alloy/Copper (I) Salts
Xu, Li-Wen,Xia, Chun-Gu,Li, Jing-Wei,Hu, Xiao-Xue
, p. 2071 - 2073 (2007/10/03)
A general, novel, ligandless and efficient method was developed for the Raney Ni-Al alloy/copper co-catalyzed formation of diaryl ethers by C-O cross-coupling reaction from aryl iodides, bromides, and even aryl chlorides with phenols.
THE CHEMISTRY OF PENTAVALENT ORGANOBISMUTH REAGENTS. PART X. STUDIES ON THE PHENYLATION AND OXIDATION OF PHENOLS
Barton, Derek H. R.,Yadav-Bhatnagar, Neerja,Finet, Jean-Pierre,Khamsi, Jamal,Motherwell, William B.,Stanforth, Stephen P.
, p. 323 - 332 (2007/10/02)
The influence of the substituents on the phenol on the regiochemistry of the arylation reactions with Ph3BiCl2 and other bismuth reagents has been studied.O-Phenylation occurs with phenols substituted with electron-withdrawing groups.Electron-donating substituted phenols undergo ortho C-phenylation.Oxidative dimerisation has been observed with 2,6-dialkyl phenols.
