Affiliation:
1. Instituto de Química Universidad Nacional Autónoma de México Circuito Exterior s/n Ciudad Universitaria Cd. Mx. 04510, 1 México
2. Centro Conjunto de Investigación en Química Sustentable UAEM-UNAM Carretera Toluca-Atlacomulco Km 14.5 C.P. 50200 Toluca Estado de México México
Abstract
AbstractA one‐pot diazotization/gold‐mediated cyclization of 2‐aminoaryl‐3‐arylpropargyl‐benzenesulfonamides is described. After diazotization, Me2SAuCl 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.
Funder
Dirección General de Asuntos del Personal Académico, Universidad Nacional Autónoma de México
Subject
General Chemistry,Catalysis,Organic Chemistry