Iron catalyzed C–C dehydrogenative coupling reaction: synthesis of arylquinones from quinones/hydroquinones

Abstract

The synthesis of arylquinones was achieved via direct oxidative C–H/C–H cross-coupling of quinones/hydroquinones with electron-rich arenes using Fe–I2–(NH4)2S2O8 system involving quinones/hydroquinones to give high yields (60–89%) of arylquinones.

Copper–iodine co-catalyzed C–H aminoalkenylation of indoles via temperature-controlled selectivity switch: facile synthesis of 2-azolyl-3-alkenylindoles

“…On the basis of the results described above and the relevant literature, 6–10 a plausible mechanism was proposed as shown in Scheme 5. Firstly, the reaction of nucleophilic 1 with I 2 affords the corresponding iodonium 1-I and 3-iodo iminium 1-II , which are electrophilically activated.…”

“…9 Very recently, a Fe-I 2 -(NH 4 ) 2 S 2 O 8 catalyzed version was developed by Dong and co-workers ( path B). 10 However, the majority of these methods involve either multistep sequences or environmentally unfriendly oxidants. Although some efficient synthetic methods for 2,3-difunctionalization of indoles via tandem reactions have been developed, aminoalkenylation of indoles has remained unexplored.…”