Highly regioselective para-methylthiolation/bridging methylenation of arylamines promoted by NH4I
Aryl methyl thioethers and methylene-bridged arylamines were synthesized via highly regioselective para-methylthiolation/bridging methylenation of arylamines using DMSO as the methylthio or methylene source in the presence of NH4I under metal-free conditions. For the substrates with both electron-donating and electron-withdrawing substituents, the reaction proceeded smoothly and gave moderate to good yields.
Xu, Yinfeng,Cong, Tiantian,Liu, Ping,Sun, Peipei
supporting information
p. 9742 - 9745
(2015/10/05)
Metallation reactions XXVII. Metallation of (methylthio)anilines
The metallation reactions of (methylthio)anilines with organolithium reagents and with the butyllithium-potassium tert-butoxide superbasic mixture are here described. The results show that the para isomer when treated with butyllithium gave a mixture of p