Oxy- and Chloroarylation Pathways in Gold-Mediated Cyclization of 2-Aminoaryl-3-arylpropargyl-benzenesulfonamides.

ABSTRACT

A one-pot diazotization/gold-mediated cyclization of 2-aminoaryl-3-arylpropargyl-benzenesulfonamides is described. After diazotization, Me2 SAuCl triggers an oxy- and/or chloroarylation of the alkyne moiety, resulting in the formation of 3-acylindoles and/or Z-3-(chloromethylene)indolines. Density Functional Theory (DFT) calculations show the significant energetic preference of both processes over an insertion pathway. Notably, a Z-3-(chloromethylene)indoline crystallized with [Cl-Au-Cl],- exhibiting Au⋅⋅⋅H-C short contacts.