Open AccessN-Aminopyridinium Ylide-Directed, Copper-Promoted Amination of sp2 C–H Bonds
Author(s) -
Se Hun Kwak,
Olafs Daugulis
Publication year - 2019
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.9b01847
Subject(s) - ylide , amination , copper , chemistry , medicinal chemistry , organic chemistry , catalysis
N -Aminopyridinium ylides are used as monodentate directing groups for copper-promoted C-H/N-H coupling of sp 2 C-H bonds with pyrazoles, imidazoles, and sulfonamides. Reactions proceed in fluorinated alcohol solvents at elevated temperatures and require use of 1.3-3 equiv of copper(II) acetate. This appears to be the first method for copper-promoted C-H/N-H coupling directed by a removable monodentate auxiliary in absence of added ligands.