Exploiting the narrow gap of rearrangement between the substituents in the vicinal disubstitution reactions of diaryliodonium salts with pyridine N-sulfonamidates.
The vicinal disubstitution reactions of diaryliodonium salts with pyridine N-sulfonamidates to give o-pyridinium anilines were fully examined. A reaction pathway of N-arylation occurring at the amidate group followed by a radical rearrangement is proposed. The electronic effects of various substituents in this radical rearrangement were investigated.
College of Chemistry and Molecular Engineering, Qingdao University of Science & Technology, Qingdao, 266042, China. Chenchao01@mails.tsinghua.edu.cn liming928@qust.edu.cn.
Yong
Y
Wang
Ming
M
Li
Lirong
L
Wen
Peng
P
Jing
Xiang
X
Su
Chao
C
Chen
D000814:Aniline Compounds / Q000138:chemical synthesis*; D017613:Iodine Compounds / Q000737:chemistry*; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry; D012492:Salts; D013449:Sulfonamides / Q000737:chemistry*
D000814:Aniline Compounds; D017613:Iodine Compounds; D011725:Pyridines; D012492:Salts; D013449:Sulfonamides; C023666:pyridine