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. 2022 Jul 26:10:941016.
doi: 10.3389/fchem.2022.941016. eCollection 2022.

Metal-free photo-induced sulfidation of aryl iodide and other chalcogenation

Shuai Mao  1 , Yahao Zhao  1 , Zixuan Luo  2 , Ruizhe Wang  1 , Bo Yuan  1 , Jianping Hu  3 , Linghao Hu  4   5 , San-Qi Zhang  1 , Xiaoxing Ye  3 , Mingliang Wang  4   5 , Zhengkai Chen  6
Affiliations

Metal-free photo-induced sulfidation of aryl iodide and other chalcogenation

Shuai Mao et al. Front Chem. .

Abstract

A photo-induced C-S radical cross-coupling of aryl iodides and disulfides under transition-metal and external photosensitizer free conditions for the synthesis of aryl sulfides at room temperature has been presented, which features mild reaction conditions, broad substrate scope, high efficiency, and good functional group compatibility. The developed methodology could be readily applied to forge C-S bond in the field of pharmaceutical and material science.

Keywords: aryl sulfides; cross-coupling; disulfides; metal-free; photo-induced.

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Conflict of interest statement

Author ZL was employed by Xi’an Changqing Chemical Group Co., Ltd. The remaining authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest.

Figures

FIGURE 1
FIGURE 1
Representative drugs containing aryl sulfide motif.
FIGURE 2
FIGURE 2
The C‐S formation methods with aryl halides and thiols/disulfides.
FIGURE 3
FIGURE 3
On-off experiment kinetic profile.
FIGURE 4
FIGURE 4
The radical trapping experiment.
FIGURE 5
FIGURE 5
Proposed reaction mechanism.
See this image and copyright information in PMC

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References

    1. Akkilagunta V. K., Kakulapati R. R. (2011). Synthesis of unsymmetrical sulfides using ethyl potassium xanthogenate and recyclable copper catalyst under ligand-free conditions. J. Org. Chem. 76, 6819–6824. 10.1021/jo200793k - DOI - PubMed
    1. Alvaro E., Hartwig J. F. (2009). Resting state and elementary steps of the coupling of aryl halides with thiols catalyzed by alkylbisphosphine complexes of palladium. J. Am. Chem. Soc. 131, 7858–7868. 10.1021/ja901793w - DOI - PMC - PubMed
    1. Amiri K., Rostami A., Rostami A. (2016b). CuFe 2 O 4 magnetic nanoparticle catalyzed odorless synthesis of sulfides using phenylboronic acid and aryl halides in the presence of S 8. New J. Chem. 40, 7522–7528. 10.1039/c6nj01434h - DOI
    1. Amiri K., Rostami A., Samadi S., Rostami A. (2016a). Cu-ZSM5 as reusable catalyst for the one-pot, odorless and ligand-free C-S bond formation. Catal. Commun. 86, 108–112. 10.1016/j.catcom.2016.07.019 - DOI
    1. Atashkar B., Rostami A., Rostami A., Zolfigol M. A. (2019). NiFe2O4 as a magnetically recoverable nanocatalyst for odourless C–S bond formation via the cleavage of C–O bond in the presence of S8 under mild and green conditions. Appl. Organomet. Chem. 33, e4691. 10.1002/aoc.4691 - DOI

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