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. 2022 Apr 12;28(21):e202200181.
doi: 10.1002/chem.202200181. Epub 2022 Mar 14.

Oxidation of BINOLs by Hypervalent Iodine Reagents: Facile Synthesis of Xanthenes and Lactones

Huaiyuan Zhang  1   2 , Thomas Wirth  1
Affiliations

Oxidation of BINOLs by Hypervalent Iodine Reagents: Facile Synthesis of Xanthenes and Lactones

Huaiyuan Zhang et al. Chemistry. .

Abstract

Xanthene derivatives have broad applications in medicines, fluorescent probes, dyes, food additives, etc. Therefore, much attention was focused on developing the synthetic methods to prepare these compounds. Binaphthyl-based xanthene derivatives were prepared through the oxidation of BINOLs promoted by the hypervalent iodine reagent iodosylbenzene (PhIO). Nine-membered lactones were obtained through a similar oxidative reaction when iodoxybenzene (PhIO2 ) was used. Additionally, one-pot reactions of BINOLs, PhIO and nucleophiles such as alcohols and amines were also investigated to provide alkoxylated products and amides in good to excellent yields.

Keywords: BINOL; hypervalent iodine reagents; lactones; oxidation; xanthenes.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Commercially available xanthene derivatives.
Scheme 1
Scheme 1
The oxidation of BINOLs to form xanthene derivatives and lactones.
Scheme 2
Scheme 2
Amines as nucleophile in the oxidation of BINOL with iodosylbenzene 2 a.
Scheme 3
Scheme 3
Synthetic utility of 3 a and 4 a.
Scheme 4
Scheme 4
Control experiments.
Scheme 5
Scheme 5
Proposed mechanisms for the formation of 3, 4 and 5.
See this image and copyright information in PMC

References

    1. None
    1. Guo S.-H., Leng T.-H., Wang K., Wang C.-Y., Shen Y.-J., Zhu W.-H., Talanta 2018, 185, 359–364; - PubMed
    1. Liu J., Chen X., Zhang Y., Gao G., Zhang X., Hou S., J. Lumin. 2018, 204, 480–484;
    1. Zhang N., Dong B., Kong X., Wang C., Song W., Lin W., J. Fluoresc. 2018, 28, 681–687; - PubMed
    1. Ebaston T. M., Rozovsky A., Zaporozhets A., Bazylevich A., Tuchinsky H., Marks V., Gellerman G., Patsenker L. D., ChemMedChem 2019, 14, 1727–1734; - PubMed

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