Categories: C-S Bond Formation >
Synthesis of phosphorothioates
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Recent Literature
The use of the iminium salt prepared from N,N-dimethylthioformamide
and Meerwein’s salt enables a direct and rapid conversion of primary and
secondary alcohols to the corresponding phosphorothiolates in good yields.
Selective reaction of primary alcohols in the presence of secondary alcohols is
possible. The reaction of secondary alcohols proceeds stereospecifically with
inversion of configuration.
H. Grounds, K. Ermanis, S. A. Newgas, M. J. Porter, J. Org. Chem.,
2017, 82, 12735-12739.
An Ir-catalyzed decarboxylative phosphorothiolation of N-hydroxyphthalimide
esters provides phosphorothioates under visible light irradiation. The reaction
tolerates a broad range of functional groups, provides sterically hindered
phosphorothioates, and enables the late stage modification of bioactive
molecules.
Y. Guo, Y. Luo, S. Mu, J. Xu, Q. Song, Org. Lett., 2021, 23,
6729-6734.
The use of diaryliodonium salts enables a direct metal-free S-arylation
of phosphorothioate diesters. The method allows for the preparation of a broad
range of S-aryl phosphorothioates as well as other related
organophosphorus compounds under simple conditions. The reaction proceeds with a
full retention of the stereogenic center at the phosphorus atom.
S. Sarkar, M. Kalek, Org. Lett., 2023, 25,
671-675.
A multicomponent reaction involving aryl boronic acids, elemental sulfur, and
P(O)H compounds provides valuable S-aryl phosphorothioates and S-aryl
phosphorodithioates in excellent yields. Moreover, this method can be easily
scaled up.
J. Xu, L. Zhang, X. Li, Y. Gao, G. Tang, Y. Zhao, Org. Lett., 2016, 18,
1100-1103.
Green methods based on copper-catalyzed multicomponent reactions enable the
synthesis of S-aryl phosphorothioates from diaryliodonium/arenediazonium
salts, elemental sulfur, and R2P(O)H compounds in very good yields at
room temperature. These transformations allow the direct formation of P-S and
C-S bonds in one reaction.
L. Zhang, P. Zhang, X. Li, J. Xu, G. Tang, Y. Zhao, J. Org. Chem.,
2016,
81, 5566-5573.
