Synthesis of N-alkoxyphthalimide derivatives via PIDA-promoted cross dehydrogenative coupling reaction

Abstract

A cross dehydrogenative coupling reaction of aryl ketones with N-hydroxyphthalimide was realized. The reactions afforded a clean and facile access to diverse N-alkoxyphthalimide derivatives in high yields (up to 99%).

2-(2,5-Dimethoxyphenoxy)isoindoline-1,3-dione

“…The ability of the phthalimide-N-oxyl (PINO) radical, which is generated from NHPI, to act as a mediator of hydrogen atom abstraction is well known, [10] but the preparative chemistry of this radical remains less studied. A number of processes are known in which the resulting PINO radical enters into reactions of C-H functionalization [11,12] or selective difunctionalization of multiple bonds [13][14][15][16]. However, direct C-H functionalization of aromatic systems with NHPI remains poorly studied and is represented by a single work [17].…”

Copper(ii)-catalyzed and acid-promoted highly regioselective oxidation of tautomerizable C(sp3)–H bonds adjacent to 3,4-dihydroisoquinolines using air (O2) as a clean oxidant

“… 1 Recently, significant efforts of chemists have been devoted to solving the issues of oxidation of C(sp 3 )–H bonds in a variety of substrates. 2 Although many oxidants can be used in the above oxidation of C(sp 3 )–H bonds, air (O 2 ) is certainly the best choice in the light of its abundance, easy availability, cheapness and eco-friendliness. On the other hand, copper is a low toxic and inexpensive transition metal.…”