Mild persubstitution of di- and tetrabrominated arenes with arylthiolate nucleophiles

作者：Del Rosso Pablo G^*; Almassio Marcela F; Bruno Mattia; Garay Raul O

来源：Tetrahedron Letters, 2010, 51(51): 6730-6733.

DOI：10.1016/j.tetlet.2010.10.069

• Selective sulfuration
• Aromatic substitution
• Persulfurated arenes
• Organic materials

A mild selective protocol was used to prepare tetrakis(2-chlorophenylthio)anthracene from tetrabromo-anthracene and sodium 2-chlorobenzenethiolate avoiding the thiolate self-attack. The uncatalyzed nucleophilic substitution of a series of mono-, di-, and tetrabrominated arenes by arylthiolate ions was attempted in mild conditions to investigate the scope of the substitution reaction regarding the size of the aromatic system as well as the number of bromine atoms. Successful reactions afforded only the persubstituted products in good purity and yield after a simple workup and chemoselectivity of Br versus Cl substituents was achieved for the tetrabromide.

• 出版日期2010-12-22