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.
College of Chemistry and Materials Science, Jiangsu Provincial Key Laboratory of Material Cycle Processes and Pollution Control, Nanjing Normal University, Nanjing 210097, China. sunpeipei@njnu.edu.cn.
Yinfeng
Y
Xu
Tiantian
T
Cong
Ping
P
Liu
Peipei
P
Sun
D000588:Amines / Q000737:chemistry*; D064751:Ammonium Compounds; D002384:Catalysis; D004583:Electrons; D008697:Methane / Q000031:analogs & derivatives*; D008745:Methylation; D015394:Molecular Structure; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013440:Sulfides / Q000737:chemistry*
D000588:Amines; D064751:Ammonium Compounds; D000644:Quaternary Ammonium Compounds; D013440:Sulfides; D008697:Methane; C582942:ammonium iodide