30752-28-4Relevant academic research and scientific papers
Pushing the Limits of Neutral Organic Electron Donors: A Tetra(iminophosphorano)-Substituted Bispyridinylidene
Hanson, Samuel S.,Doni, Eswararao,Traboulsee, Kyle T.,Coulthard, Graeme,Murphy, John A.,Dyker, C. Adam
, p. 11236 - 11239 (2016)
A new ground-state organic electron donor has been prepared that features four strongly π-donating iminophosphorano substituents on a bispyridinylidene skeleton. Cyclic voltammetry reveals a record redox potential of ?1.70 V vs. saturated calomel electrode (SCE) for the couple involving the neutral organic donor and its dication. This highly reducing organic compound can be isolated (44 %) or more conveniently generated in situ by a deprotonation reaction involving its readily prepared pyridinium ion precursor. This donor is able to reduce a variety of aryl halides, and, owing to its redox potential, was found to be the first organic donor to be effective in the thermally induced reductive S N bond cleavage of N,N-dialkylsulfonamides, and reductive hydrodecyanation of malonitriles.
Base-Mediated O-Arylation of Alcohols and Phenols by Triarylsulfonium Triflates
Ming, Xiao-Xia,Tian, Ze-Yu,Zhang, Cheng-Pan
supporting information, p. 3370 - 3379 (2019/11/03)
A mild and efficient protocol for O-arylation of alcohols and phenols (ROH) by triarylsulfonium triflates was developed under transition-metal-free conditions. Various alcohols, including primary, secondary and tertiary, and phenols bearing either electron-donating or electron-withdrawing groups on the aryl rings were smoothly converted to form the corresponding aromatic ethers in moderate to excellent yields. The reactions were conducted at 50 or 80 °C for 24 h in the presence of a certain base and showed good functional group tolerance. The base-mediated arylation with asymmetric triarylsulfonium salts could selectively transfer the aryl groups of sulfoniums to ROH, depending on their inherent electronic nature. The mechanistic studies revealed that the reaction might proceed through the nucleophilic attack of the in situ formed alkoxy or phenoxy anions at the aromatic carbon atoms of the C?S bonds of triarylsulfonium cations to furnish the target products.
