Photochemical pincer catalyzed reductive cyclisation towards indolines and oxindoles

Abstract

An organophotocatalytic method has been described towards the synthesis of indolines and oxindoles starting from unusual α-chloro amide and N-(2-chlorophenyl)-N-alkyl methacrylamide substrates. This marks a notable improvement since the earlier syntheses utilized iridium and gold catalysts, and involved C-I or C-Br bond cleavage as the initial step. Our photocatalyst is a pincer ligand that can be easily deprotonated to make a very strong reducing agent. The reductive cleavage of the carbon-chloride bond, and subsequent 5-exo-trig ring cyclization, followed by hydrogen atom abstraction prepare desired heterocycles under very mild reaction conditions. An atom economic use of KOtBu has been shown to demonstrate the unusual trifunctional role of the latter.