2-Fluoro-5-(trifluoromethyl)aniline
was found to be a suitable
monodentate transient directing group (MonoTDG) to enable Ru(II)-catalyzed
intermolecular direct ortho-C(sp2)–H
imidation of benzaldehydes. N-Tosyloxyphthalimide
was used as an alternative azide-free amidation reagent to achieve
high efficiency and good functional group tolerance. Moreover, the
reaction could be enlarged to gram scale, and the amidated product
could be readily converted into useful quinazoline and fused isoindolinone
scaffolds by one-step derivatization.
An expeditious construction of an unsymmetrical tertiary
9-fluorenol
skeleton was accomplished starting from readily available α-ketoester
and aryl iodide. Inexpensive commercially available substituted aniline
was utilized as a potent monodentate transient directing group (TDG)
to assist palladium-catalyzed direct ortho-C–H arylation and
tandem dual C–H activation of α-ketoesters to form two
carbon–carbon bonds. To demonstrate practical applications,
the reaction was enlarged to the gram scale, and subsequent one-step
derivatization allowed facile access to structurally diversified useful
derivatives. A series of control experiments were carried out to shed
light on the possible catalytic mechanism.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.