6738-04-1Relevant articles and documents
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.
Competing Pathways in O-Arylations with Diaryliodonium Salts: Mechanistic Insights
Stridfeldt, Elin,Lindstedt, Erik,Reitti, Marcus,Blid, Jan,Norrby, Per-Ola,Olofsson, Berit
, p. 13249 - 13258 (2017/09/12)
A mechanistic study of arylations of aliphatic alcohols and hydroxide with diaryliodonium salts, to give alkyl aryl ethers and diaryl ethers, has been performed using experimental techniques and DFT calculations. Aryne intermediates have been trapped, and additives to avoid by-product formation originating from arynes have been found. An alcohol oxidation pathway was observed in parallel to arylation; this is suggested to proceed by an intramolecular mechanism. Product formation pathways via ligand coupling and arynes have been compared, and 4-coordinated transition states were found to be favored in reactions with alcohols. Furthermore, a novel, direct nucleophilic substitution pathway has been identified in reactions with electron-deficient diaryliodonium salts.
The Suzuki-Miyaura Coupling of Nitroarenes
Yadav, M. Ramu,Nagaoka, Masahiro,Kashihara, Myuto,Zhong, Rong-Lin,Miyazaki, Takanori,Sakaki, Shigeyoshi,Nakao, Yoshiaki
supporting information, p. 9423 - 9426 (2017/07/24)
Synthesis of biaryls via the Suzuki-Miyaura coupling (SMC) reaction using nitroarenes as an electrophilic coupling partners is described. Mechanistic studies have revealed that the catalytic cycle of this reaction is initiated by the cleavage of the aryl-nitro (Ar-NO2) bond by palladium, which represents an unprecedented elemental reaction.
