Cationic N‑Heterocyclic Carbene Copper-Catalyzed [1,3]-Alkoxy Rearrangement of N-Alkoxyanilines

The [1,3]-alkoxy rearrangement reactions of N-alkoxyanilines were efficiently catalyzed by cationic N-heterocyclic carbene (NHC)-Cu catalysts in affording 2-alkoxyaniline derivatives in good to excellent yields with high functional group compatibility. For N-alkoxyanilines having an electron-withdra...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2017-06, Vol.19 (12), p.3059-3062
Main Authors: Nakamura, Itaru, Jo, Takeru, Ishida, Yasuhiro, Tashiro, Hiroki, Terada, Masahiro
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The [1,3]-alkoxy rearrangement reactions of N-alkoxyanilines were efficiently catalyzed by cationic N-heterocyclic carbene (NHC)-Cu catalysts in affording 2-alkoxyaniline derivatives in good to excellent yields with high functional group compatibility. For N-alkoxyanilines having an electron-withdrawing substituent at the meta-position, the alkoxy group selectively migrated to the more hindered ortho-position. In contrast, the alkoxy group migrated to the less hindered ortho-position for N-alkoxyanilines having an electron-donating substituent. Mechanistic studies suggest that the rearrangement reactions proceed via an intramolecular route.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b01110