Tertiary anilines can be prompted to react with N‐aryl‐ and N‐benzylmaleimides to form tetrahydroquinoline products under photocatalysis using visible light irradiation, the ruthenium or iridium complexes Ru(bpy)3Cl2 or Ir(ppy)2(dtbbpy)PF6 as catalyst, and air as terminal oxidant.

2-Electron-withdrawing-group-substituted 2-bromoanilides can be converted to the corresponding 3,3-disubstituted oxindoles with high efficiency under visible light irradiation by using fac-Ir(ppy)(3) as the photoredox catalyst. This protocol is suitable for the synthesis of oxindoles with chloro and bromo atoms attached to the phenyl ring.

Phenyliodine(III) bis(trifluoroacetate) (PIFA) can effect the intramolecular oxidative coupling of substituted 4-hydroxyphenyl-N-phenylbenzamides. The transformations could be realized in a catalytic manner by using iodobenzene as catalyst and m-chloroperoxybenzoic acid or urea·H 2 O 2 as terminal oxidant. This reaction constitutes an efficient method for the synthesis of spirooxindoles.

The cyclization of α‐bromoanilides bearing an electron‐withdrawing group in α‐position towards oxindoles (II), (IV), (VI)/(VII) and (IX) is efficiently achieved under visible light irradiation in the presence of photoredox catalyst Ir(ppy)3.

A series of spirooxindoles (II) is readily prepared by an intramolecular oxidative coupling reaction of benzamides (I). The analogous reaction of amides (VI) gives rise to spirodihydroquinolones (VII) in moderate yields. -(YU, Z.; JU, X.; WANG, J.; YU*, W.; Synthesis 2011, 6, 860-866, http://dx.