Categories: C-S Bond Formation >
Synthesis of phosphorothiolates
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.
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.
