Open AccessCobalt-Catalyzed C–H Activation/Annulation of Benzamides with Fluorine-Containing Alkynes: A Route to 3- and 4-Fluoroalkylated Isoquinolinones
Author(s) -
Tatsuya Kumon,
Jianyan Wu,
Miroku Shimada,
Shigeyuki Yamada,
Tomohiro Agou,
Hiroki Fukumoto,
Toshio Kubota,
Gerald B. Hammond,
Tsutomu Konno
Publication year - 2021
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.1c00080
Subject(s) - annulation , chemistry , catalysis , structural isomer , cobalt , regioselectivity , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry
The C-H activation/annulation reaction of various benzamides with fluoroalkylated alkynes in the presence of a Co(acac) 2 ·2H 2 O catalyst proceeded very smoothly to give the corresponding 3- and 4-fluoroalkylated isoquinolinones in excellent yields with approximately 70% regioselectivities. These regioisomers could be successfully separated and obtained in pure form. Major or minor regioisomers were determined as 4- or 3-fluoroalkylated isoquinolinones, respectively, based on X-ray crystallographic analyses.