57772-59-5Relevant academic research and scientific papers
Singlet Oxygen Generation from a Water-Soluble Hypervalent Iodine(V) Reagent AIBX and H2O2: An Access to Artemisinin
Hu, Ze-Nan,Shen, Hui-Jie,Zhang, Chi
, (2021/06/21)
Herein, we report an efficient method for the chemical generation of 1O2 by treatment of H2O2 with AIBX, a highly water-soluble, bench-stable, recyclable hypervalent iodine(V) reagent developed by our group. The generation of 1O2 was confirmed by the following results: (1) capture of 1O2 with the sodium salt of anthracene-9,10-bis(ethanesulfonate) produced the corresponding endoperoxide and (2) TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy) produced by the oxidation of 2,2,6,6-tetramethylpiperidine with 1O2 generated using the AIBX/H2O2 system was detected by electron spin resonance spectroscopy. To illustrate the potential utility of this method for organic synthesis, we used the AIBX/H2O2 system to perform typical reactions of 1O2: [2 + 2]/[4 + 2] cycloadditions, Schenck ene reactions, and heteroatom oxidation reactions, which afforded the corresponding products in high yields. Moreover, we used the method to synthesize the antimalarial drug artemisinin. Finally, we demonstrated that AIBX could be regenerated after the reaction by means of a workup involving extraction and removal of water to obtain a precursor of AIBX, which could then be re-oxidized.
Design, synthesis, structure, and dehydrogenation reactivity of a water soluble o-iodoxybenzoic acid derivative bearing a trimethylammonium group
Cui, Li-Qian,Dong, Zhi-Lei,Liu, Kai,Zhang, Chi
, p. 6488 - 6491 (2012/02/02)
5-Trimethylammonio-1, 3-dioxo-1, 3-dihydro-1λ5-benzo[d][1, 2]iodoxol-1-ol anion (AIBX 1a), an o-iodoxybenzoic acid (IBX) derivative having the trimethylammonium moiety on its phenyl ring, possesses very good solubility in water and distinct oxidative properties from IBX, which is demonstrated in the oxidation of various β-keto esters to the corresponding dehydrogenated products using water as cosolvent. The regeneration of AIBX 1a can be easily realized from the reaction mixture due to its good water solubility.2011 American Chemical Society.
