Exploiting the narrow gap of rearrangement between the substituents in the vicinal disubstitution reactions of diaryliodonium salts with pyridine N-sulfonamidates

Yong Wang; Ming Li; Lirong Wen; Peng Jing; Xiang Su; Chao Chen

doi:10.1039/c4ob01744g

Exploiting the narrow gap of rearrangement between the substituents in the vicinal disubstitution reactions of diaryliodonium salts with pyridine N-sulfonamidates

Org Biomol Chem. 2015 Jan 21;13(3):751-63. doi: 10.1039/c4ob01744g.

Authors

Yong Wang¹, Ming Li, Lirong Wen, Peng Jing, Xiang Su, Chao Chen

Affiliation

¹ College of Chemistry and Molecular Engineering, Qingdao University of Science & Technology, Qingdao, 266042, China. Chenchao01@mails.tsinghua.edu.cn liming928@qust.edu.cn.

PMID: 25382109
DOI: 10.1039/c4ob01744g

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aniline Compounds / chemical synthesis*
Iodine Compounds / chemistry*
Molecular Structure
Pyridines / chemistry
Salts
Sulfonamides / chemistry*

Substances

Aniline Compounds
Iodine Compounds
Pyridines
Salts
Sulfonamides
pyridine