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Oxy- and Chloroarylation Pathways in Gold-Mediated Cyclization of 2-Aminoaryl-3-arylpropargyl-benzenesulfonamides
Howard Díaz-Salazar1, Ignacio Medina-Mercado1, Román Salvador-Reyes1
1Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior s/n, Ciudad Universitaria, Cd. Mx. 04510, 1, México.
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.
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