1706-12-3Relevant articles and documents
Oxidation of m-Phenoxytoluene with Ceric Trifluoroacetate
Marrocco, Matt,Brilmyer, George
, p. 1487 - 1491 (1983)
Ceric trifluoroacetate in aqueous trifluoroacetic acid has been found to be especially effective for the oxidation of activated toluenes to the corresponding aldehydes.Ceric ion is consumed in stoichiometric amounts but can be regenerated electrochemically at high current efficiencies (95 percent).A detailed study of the oxidation of m-phenoxytoluene to m-phenoxybenzaldehyde is presented.A study of the reaction mechanism, which involves both cations and radical cations, led to a choise of cosolvents which stabilize these intermediates and thus increase the yield of aldehyde formation.
Ligand- and Counterion-Assisted Phenol O-Arylation with TMP-Iodonium(III) Acetates
Kikushima, Kotaro,Miyamoto, Naoki,Watanabe, Kazuma,Koseki, Daichi,Kita, Yasuyuki,Dohi, Toshifumi
supporting information, p. 1924 - 1928 (2022/03/27)
High reactivity of trimethoxyphenyl (TMP)-iodonium(III) acetate for phenol O-arylation was achieved. It was first determined that the TMP ligand and acetate anion cooperatively enhance the electrophilic reactivity toward phenol oxygen atoms. The proposed method provides access to various diaryl ethers in significantly higher yields than the previously reported techniques. Various functional groups, including aliphatic alcohol, boronic ester, and sterically hindered groups, were tolerated during O-arylation, verifying the applicability of this ligand- and counterion-assisted strategy.
L-Proline N-oxide dihydrazides as an efficient ligand for cross-coupling reactions of aryl iodides and bromides with amines and phenols
Ding, Zhiqiang,Nie, Nan,Chen, Tian,Meng, Lingxin,Wang, Gongshu,Chen, Zhangpei,Hu, Jianshe
supporting information, (2020/12/21)
A novel catalytic system based on L-proline N-oxide/CuI was developed and applied to the cross-coupling reactions of various N- and O- nucleophilic reagents with aryl iodides and bromides. This strategy featured in the employment of an-proline derived dihydrazides N-oxide compound as the superior supporting ligand. By using this protocol, a variety of products, including N-arylimidazoles, N-arylpyrazoles, N-arylpyrroles, N-arylamines, and aryl ethers, were synthesized with up to 99% yield.