64357-40-0Relevant academic research and scientific papers
Copper-Catalyzed Oxidative Fragmentation of Alkynes with NFSI Provides Aryl Ketones
Chen, Hanfei,Cheng, Hao,Huang, Yifan,Jin, Chaochao,Song, Weihan,Tan, Chen,Tan, Jiajing,Tang, Lin,Yang, Fang,Zhang, Shuaifei
supporting information, (2020/11/03)
A copper-catalyzed oxidative cleavage reaction of alkynes using NFSI and TBHP was described. Various terminal and internal alkyne substrates were employed to render quick access to aryl ketone products in moderate to good yields. NFSI not only functioned as N-centered radical precursors but also engaged in the aryl group migration. Mechanistic studies also suggested the important role of water in the title reactions.
Nickel-Catalyzed C-O Bond-Cleaving Alkylation of Esters: Direct Replacement of the Ester Moiety by Functionalized Alkyl Chains
Liu, Xiangqian,Jia, Jiaqi,Rueping, Magnus
, p. 4491 - 4496 (2017/07/24)
Two efficient protocols for the nickel-catalyzed aryl-alkyl cross-coupling reactions using esters as coupling components have been established. The methods enable the selective oxidative addition of nickel to acyl C-O and aryl C-O bonds and allow the aryl-alkyl cross-coupling via decarbonylative bond cleavage or through cleavage of a C-O bond with high efficiency and good functional group compatibility. The protocols allow the streamlined, unconventional utilization of widespread ester groups and their precursors, carboxylic acids and phenols, in synthetic organic chemistry.
Tetraorganylborate salts as convenient precursors for photogeneration of tertiary amines
Sarker, Ananda M.,Lungu, Adrian,Mejiritski, Alexander,Kaneko, Yuji,Neckers, Douglas C.
, p. 2315 - 2331 (2007/10/03)
Photoreactions of p-(benzoyl)benzyl trisubstituted ammonium tetraorganylborate salts for the generation of tertiary amines in solution and rigid matrices are described. Structural modification of the complexes allows study of the influence of steric and electronic effects on the photogeneration of amines. Flash photolysis, cyclic voltammetry and product analysis indicate that single electron transfer from borate to excited benzophenone is followed by homolytic C-N bond cleavage. Photoliberation of the tertiary amine is controlled by the rate of the electron transfer reaction.
Photoinduced Inter- and Intra-Ion-Pair Electron Transfer Reactions in N-(p-Benzoylbenzyl)-N,N,N-tri-n-butylammonium Triphenyl-n-butylborate and -Gallate Salts
Hassoon, S.,Sarker, A.,Polykarpov, A. Y.,Rodgers, N. A. J.,Neckers, D. C.
, p. 12386 - 12393 (2007/10/03)
The protoreduction of N-(p-benzoylbenzyl)-N,N,N-tri-n-butylammonium triphenyl-n-butylborate (1) and gallate (2) was studied using nano- and picosecond laser flash photolysis.An electron transfer reaction from the borate or the galate counteranion to the excited triplet state of the benzophenone moiety (BP*3) was demonstrated.This reaction leads to the formation of benzophenone radical anion (6) and the boranyl radical, the latter of which dissociates rapidly to form butyl radical.The electron transfer rate was found to depend on the polarity of the solvent.In neat benzene, the short lifetime of the triplet obtained (300 +/- 150 ps) indicates an intramolecular process and that the compounds exist as tight ion pairs.The addition of 1percent MeCN increases the triplet lifetime up to 1.2 ns.The formation of a solvent-separated ion pair was suggested in this solvent mixture.However, in the polar solvent MaCN, 1 and 2 exist partially as free ions as determined by their dissociation constants.A diffusion-controlled intermolecular electron transfer process was shown in this solvent.The p-benzyloxybenzyl radical (BPCH2.), most likely formed by the C-N cleavage bond in the radical anion (6), was identified as an intermediate in the reaction pathway.After the initial electron transfer reaction, this produced tributylamine.The quantum yield obtained for the reaction of 1, 1E-2 M in MeCN, is 0.5 +/- 0.05.Triplet quenching as well as coupling of the radical anion (6) with the butyl radical deriving from decomposition of the borate was suggested to complete with the C-N cleavage reaction.
Norrish Type I and Type II Reactions of Ketones as Photochemical Probes of the Interior of Zeolites
Ramamurthy, V.,Corbin, D. R.,Eaton, D. F.
, p. 5269 - 5278 (2007/10/02)
The Norrish type I and type II reactions of alkylbenzoin ethers, alkyldeoxybenzoins and α-alkyldibenzyl ketones included within the microporous structures of zeolites X and Y have been investigated.Product distributions varied significantly from that observed in benzene.In addition, it differed between various alkali-metal cation-exchanged samples.These variations are interpreted to result from the restriction offered by the zeolite micropores on the motions of the adsorbed organic molecule.Although this study is restricted to ketones, the knowledge gained is expected to be of general value.
