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Rongalite-promoted transition metal-free synthesis of S-aryl phosphorothioates

Min-xiao Xu 1
Min-xiao Xu
, 
Kai-Ming Zhang 1, 2
Kai-Ming Zhang
1 Jiangsu Police Institute, Nanjing, P.R. China
10.1016/j.mencom.2022.05.033
Published 2022-04-29
Communication , Volume 32, Issue 3, 390-392
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Xu M., Zhang K. Rongalite-promoted transition metal-free synthesis of S-aryl phosphorothioates // Mendeleev Communications. 2022. Vol. 32. No. 3. pp. 390-392.
GOST all authors (up to 50) Copy
Xu M., Zhang K. Rongalite-promoted transition metal-free synthesis of S-aryl phosphorothioates // Mendeleev Communications. 2022. Vol. 32. No. 3. pp. 390-392.
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TY - JOUR
DO - 10.1016/j.mencom.2022.05.033
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.05.033
TI - Rongalite-promoted transition metal-free synthesis of S-aryl phosphorothioates
T2 - Mendeleev Communications
AU - Xu, Min-xiao
AU - Zhang, Kai-Ming
PY - 2022
DA - 2022/04/29
PB - Mendeleev Communications
SP - 390-392
IS - 3
VL - 32
ER -
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@article{2022_Xu,
author = {Min-xiao Xu and Kai-Ming Zhang},
title = {Rongalite-promoted transition metal-free synthesis of S-aryl phosphorothioates},
journal = {Mendeleev Communications},
year = {2022},
volume = {32},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.05.033},
number = {3},
pages = {390--392},
doi = {10.1016/j.mencom.2022.05.033}
}
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Xu, Min-xiao, and Kai-Ming Zhang. “Rongalite-promoted transition metal-free synthesis of S-aryl phosphorothioates.” Mendeleev Communications, vol. 32, no. 3, Apr. 2022, pp. 390-392. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.05.033.
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Keywords

aryl halides
arylation
phosphorothioates
radical process
rongalite
sulfur

Abstract

The improved procedure for the synthesis of S-aryl phosphorothioates from dialkyl phosphites (H-phosphonates), aryl iodides and elemental sulfur deals with the application of rongalite (sodium hydroxy-methanesulfinate) as the radical promoter. The reactions proceeded smoothly to give S-aryl phosphorothioates in good yields.

References

1.
Synthesis of Phosphorus and Sulfur Heterocycles via Ring-Closing Olefin Metathesis
McReynolds M.D., Dougherty J.M., Hanson P.R.
Chemical Reviews, 2004
3.
Design, synthesis and biological evaluation of organophosphorous-homodimers as dual binding site acetylcholinesterase inhibitors
Xie R., Zhao Q., Zhang T., Fang J., Mei X., Ning J., Tang Y.
Bioorganic and Medicinal Chemistry, 2013
5.
10.1016/j.mencom.2022.05.033_b0025
Artem’ev
Synthesis, 2017
6.
10.1016/j.mencom.2022.05.033_b0030
Artem’ev
Eur. J. Org. Chem., 2010
9.
New benzotriazole-based reagents for the phosphonylation of various N-, O-, and S-nucleophiles
Panmand D.S., Tiwari A.D., Panda S.S., Monbaliu J.M., Beagle L.K., Asiri A.M., Stevens C.V., Steel P.J., Hall C.D., Katritzky A.R.
Tetrahedron Letters, 2014
11.
A scalable electrochemical dehydrogenative cross-coupling of P(O)H compounds with RSH/ROH
Li Y., Yang Q., Yang L., Lei N., Zheng K.
Chemical Communications, 2019
12.
Phosphorothiolation of Aryl Boronic Acids Using P(O)H Compounds and Elemental Sulfur
Xu J., Zhang L., Li X., Gao Y., Tang G., Zhao Y.
Organic Letters, 2016
14.
Magnetically recyclable Cu-BTC@Fe3O4 composite-catalyzed C(aryl)–S–P bond formation using aniline, P(O)H compounds and sulfur powder
Wang L., Yang S., Chen L., Yuan S., Chen Q., He M., Zhang Z.
Catalysis Science and Technology, 2017
15.
Iodide‐Catalyzed Phosphorothiolation of Heteroarenes Using P(O)H Compounds and Elemental Sulfur
Shi S., Chen J., Zhuo S., Wu Z., Fang M., Tang G., Zhao Y.
Advanced Synthesis and Catalysis, 2019
17.
Radicals in Organic Synthesis, eds. P. Renaud and M. P. Sibi, Wiley, Weinheim, 2001.
18.
Radicals: Reactive Intermediates with Translational Potential
Yan M., Lo J.C., Edwards J.T., Baran P.S.
Journal of the American Chemical Society, 2016
21.
Visible Light Mediated Photoredox Catalytic Arylation Reactions
Ghosh I., Marzo L., Das A., Shaikh R., König B.
Accounts of Chemical Research, 2016
22.
The electron is a catalyst
Studer A., Curran D.P.
Nature Chemistry, 2014
23.
Organic Electron Donors as Powerful Single-Electron Reducing Agents in Organic Synthesis
Broggi J., Terme T., Vanelle P.
Angewandte Chemie - International Edition, 2013
25.
Rongalite: A Useful Green Reagent in Organic Synthesis
Kotha S., Khedkar P.
Chemical Reviews, 2011