Transient Formation of Hydrogen Tetraoxide from Hydrogen Peroxide with Bis(trifluoroacetoxyiodo)benzene: A Chemical Generator of Singlet Oxygen for Organic Synthesis.

Çatir, Mustafa; Kılıç, Hamdullah

doi:10.1002/chin.200341052

Cited by 1 publication

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“…Hypervalent iodine reagents have drawn considerable attention not only because of their richly varied reactivity but also because they are stable, easy to handle, and environmentally benign . In a previously reported work, H 2 O 2 has been used in combination with a hypervalent iodine reagent, either PhIO 2 or PhI(OCOCF 3 ) 2 , for the generation of 1 O 2 . However, the yields of 1 O 2 (46% and 55%, respectively) are only moderate, which limits the synthetic utility of these combinations.…”

Section: Introductionmentioning

confidence: 99%

Singlet Oxygen Generation from a Water-Soluble Hypervalent Iodine(V) Reagent AIBX and H₂O₂: An Access to Artemisinin

Shen

Zhang

2021

J. Org. Chem.

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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.

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Section: Introductionmentioning

confidence: 99%

Singlet Oxygen Generation from a Water-Soluble Hypervalent Iodine(V) Reagent AIBX and H₂O₂: An Access to Artemisinin

Shen

Zhang

2021

J. Org. Chem.

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Transient Formation of Hydrogen Tetraoxide from Hydrogen Peroxide with Bis(trifluoroacetoxyiodo)benzene: A Chemical Generator of Singlet Oxygen for Organic Synthesis.

Abstract: For Abstract see ChemInform Abstract in Full Text.

Cited by 1 publication

References 8 publications

Singlet Oxygen Generation from a Water-Soluble Hypervalent Iodine(V) Reagent AIBX and H₂O₂: An Access to Artemisinin

Singlet Oxygen Generation from a Water-Soluble Hypervalent Iodine(V) Reagent AIBX and H₂O₂: An Access to Artemisinin

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Transient Formation of Hydrogen Tetraoxide from Hydrogen Peroxide with Bis(trifluoroacetoxyiodo)benzene: A Chemical Generator of Singlet Oxygen for Organic Synthesis.

Abstract: For Abstract see ChemInform Abstract in Full Text.

Cited by 1 publication

References 8 publications

Singlet Oxygen Generation from a Water-Soluble Hypervalent Iodine(V) Reagent AIBX and H2O2: An Access to Artemisinin

Singlet Oxygen Generation from a Water-Soluble Hypervalent Iodine(V) Reagent AIBX and H2O2: An Access to Artemisinin

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Singlet Oxygen Generation from a Water-Soluble Hypervalent Iodine(V) Reagent AIBX and H₂O₂: An Access to Artemisinin

Singlet Oxygen Generation from a Water-Soluble Hypervalent Iodine(V) Reagent AIBX and H₂O₂: An Access to Artemisinin