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Sulfur as directing group in C-C, C-S and C-O bond forming reactions through CH bond activation: Ru-catalysed hydroarylation and Cu-mediated acetoxythiolation of internal alkynes

AutorUrriolabeitia, Esteban P. ; Villuendas, Pedro
Fecha de publicación2015
CitaciónOMCOS18 (2015)
ResumenThe use of directing groups to achieve high selectivities in metal-mediated organic synthesis through C-H bond activation is a well-established methodology. The choice and design of the directing group is not a trivial task since, in order to reach the maximal atom economy, it is usually incorporated to the target molecular skeleton. N- and O-directing groups have been widely used in a variety of processes, being particularly relevants in the synthesis of N- or O-heterocycles. However, the use of S-directing groups in the synthesis of S-heterocycles has been much less studied, in spite of the fact that S-containing molecules are building blocks of a large number of drug compounds, either used in agrochemical applications or with pharmacological activity. Probably the thiophilicity of transition metals, and the unavoidable deactivation of the catalysts, is closely related with this scarce representation; at the same time, however, it is an additional challenge for the in-depth study of these systems. Aiming to provide new pathways for the synthesis of S-heterocycles we have investigated the reactivity of different S-containing species. We found that benzylthioethers react with internal alkynes, catalysed by [Ru(cymene)Cl2]2, to give the ortho-alkenylated species by hydroarylation using sulfur as the directing group. However, the formation of the S-heterocycle was not observed. The increase of the charge at the S atom changed dramatically the reactivity, instead of promoting the ring closure. Thus, benzylthiolates and thiophenolates react with internal alkynes and stoichiometric amounts of Cu(OAc)2 to give the acetoxy-thiolated cross-coupled species as the only products of double addition to the triple C-C bond.
DescripciónResumen del póster presentado al Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS) IUPAC International Symposium, celebrado en Sitges-Barcelona (España) del 28 de junio al 2 de julio de 2015.
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