64248-63-1Relevant articles and documents
Diazaphospholene-Catalyzed Hydrodefluorination of Polyfluoroarenes with Phenylsilane via Concerted Nucleophilic Aromatic Substitution
Cheng, Jin-Pei,Yang, Jin-Dong,Zhang, Jingjing,Zhao, Xiao
supporting information, (2022/01/03)
The metal-free catalytic C-F bond activation of polyfluoroarenes was achieved with diazaphospholene as the catalyst and phenylsilane as the terminal reductant. Density functional theory calculations suggested a concerted nucleophilic aromatic substitution mechanism.
Palladium-Catalyzed Cyanation under Mild Conditions: A Case Study to Discover Appropriate Substrates among Halides and Pseudohalides
Rajendra, Merla Arjuna,Sunil,Sajith, Ayyiliath Meleveetil,Joy, Muthipeedika Nibin,Bakulev, Vasiliy A.,Haridas, Karickal Raman
supporting information, p. 1629 - 1633 (2020/09/15)
A case study has been effectively carried out to identify a suitable substrate among halides and pseudohalides for the palladium-catalyzed cyanation reactions under mild conditions. Among the various substrates considered for evaluation, aryl pentafluorobenzenesulfonates and nonaflates were identified to be the best substrates when compared to corresponding halides and pseudohalides. The substoichiometric use of nontoxic, environmentally benign potassium hexacyanoferrate as a cyanide source and exceptionally milder conditions further highlights the significance of the protocol developed. A wide range of electronically biased and sterically challenging substrates provided the corresponding the nitriles in good to excellent yields.
Solvent-Free Aerobic Oxidation of Alcohols to Nitriles Catalyzed by Copper Iodide in Combination with a Quaternary Ammonium Modified TEMPO
Zhang, Yuecheng,Huang, Rong,Gao, Baosheng,Zhao, Jiquan
, p. 220 - 228 (2016/02/23)
A catalytic system consisting of N,N-dimethyl-(4-(2,2,6,6-tetramethyl-1-oxyl-4-piperidoxyl)butyl)dodecyl ammonium bromide (TEMPO-Q), CuI and 2,2′-bipyridine was established. This catalytic system (CuI/bpy/TEMPO-Q) showed high activity and good to excellent selectivity in the oxidative conversion of various alcohols to the corresponding nitriles with molecular oxygen as terminal oxidant and aqueous ammonia as nitrogen source under solvent-free conditions. Besides, the catalytic system also offers the advantages of simplified workup procedure. This protocol thus represents a greener pathway for the synthesis of nitriles from alcohols. Graphical Abstract: TEMPO-Q, a compound with both a TEMPO and a quaternary ammonium moieties, in combination with copper iodide and 2,2′-bipyridine as a catalytic system performed well in the oxidation of alcohols to nitriles with molecular oxygen as terminal oxidant in aqueous ammonia under solvent-free conditions. The catalytic system not only offers the advantages of simplified workup procedure, but also has high activity and selectivity due to the phase transfer catalysis of TEMPO-Q[Figure not available: see fulltext.]