A synthesis of novel (arylthio-ethylidene)indolin-2-one derivatives via S-arylation of oxoindolin-ethanethiolates with aryl halides

In recent years, Ullmann-type reactions have grown into a versatile tool for access to C−X (X = C, N, O, S, etc.) bonds.1 Although several palladium, nickel, and cobalt catalysts have proven to be highly effective in such coupling processes,2 copper reagents are favorable catalytic systems for C-X bond-forming reactions due to their low cost, low toxicity, and good functional group tolerance.3 Among various cross-coupling reactions, S-arylation is comparatively less studied. However, given the prevalence of C-S bonds in a wide range of pharmaceutical compounds and polymeric materials, it is desirable to find novel catalytic procedures that provide efficient access to such useful organic products. In this investigation, we have reported a practical procedure for the copper-catalyzed S-arylation of triethylammonium [2-oxo-1-(2-oxo-1,2-dihydro-3H-indol-3-ylidene)-2-arylethyl]sulfides, which provides a new route to the synthesis of (Z/E)-3-(2-oxo-2-aryl-1-(arylthio)ethylidene)indolin-2-one derivatives in good yields.

Keywords:

Cu(I) iodide , S-Arylation , aryl halides , 1-aryl-2-thiocyanatoethan-1-ones ,