The first nucleophilic C-H perfluoroalkylation of aromatic compounds via (arene)tricarbonylchromium complexes

Natalia V Kirij; Andrey A Filatov; Gleb Yu Khrapach; Yurii L Yagupolskii

doi:10.1039/c6cc09905j

The first nucleophilic C-H perfluoroalkylation of aromatic compounds via (arene)tricarbonylchromium complexes

Chem Commun (Camb). 2017 Feb 9;53(13):2146-2149. doi: 10.1039/c6cc09905j.

Authors

Natalia V Kirij¹, Andrey A Filatov¹, Gleb Yu Khrapach¹, Yurii L Yagupolskii¹

Affiliation

¹ Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanskaya Street, 02660, Kiev, Ukraine. yagupolskii@ioch.kiev.ua.

PMID: 28138681
DOI: 10.1039/c6cc09905j

Abstract

The first nucleophilic perfluoroalkylation of arenes is based on the arene π-system activation via (η⁶-arene)tricarbonylchromium complexes. Perfluoroalkyl anions generated from Me₃SiR_F and a fluoride ion source [Me₄N]F exclusively attack the arene ligand under mild conditions. The formed negatively charged analogs of Meisenheimer adducts readily undergo a one-pot oxidation to perfluoroalkyl arenes.