TY - JOUR
T1 - Mechanistic Insights into the FeCl3-Catalyzed Oxidative Cross-Coupling of Phenols with 2-Aminonaphthalenes
AU - Vershinin, Vlada
AU - Forkosh, Hagit
AU - Ben-Lulu, Mor
AU - Libman, Anna
AU - Pappo, Doron
N1 - Publisher Copyright:
© 2021 American Chemical Society. All rights reserved.
PY - 2021/1/1
Y1 - 2021/1/1
N2 - The selective FeCl3-catalyzed oxidative cross-coupling reaction between phenols and primary, secondary, and tertiary 2-aminonaphthalene derivatives was investigated. The generality of this scalable method provides a sustainable alternative for preparing N,O-biaryl compounds that are widely used as ligands and catalysts. Based on a comprehensive kinetic investigation, a catalytic cycle involving a ternary complex that binds to both the coupling partners and the oxidant during the key oxidative coupling step is postulated. Furthermore, the studies showed that the reaction is regulated by off-cycle acid-base and ligand exchange processes.
AB - The selective FeCl3-catalyzed oxidative cross-coupling reaction between phenols and primary, secondary, and tertiary 2-aminonaphthalene derivatives was investigated. The generality of this scalable method provides a sustainable alternative for preparing N,O-biaryl compounds that are widely used as ligands and catalysts. Based on a comprehensive kinetic investigation, a catalytic cycle involving a ternary complex that binds to both the coupling partners and the oxidant during the key oxidative coupling step is postulated. Furthermore, the studies showed that the reaction is regulated by off-cycle acid-base and ligand exchange processes.
UR - http://www.scopus.com/inward/record.url?scp=85097900553&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.0c00874
DO - 10.1021/acs.joc.0c00874
M3 - Article
C2 - 33296193
AN - SCOPUS:85097900553
SN - 0022-3263
VL - 86
SP - 79
EP - 90
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 1
ER -