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C-H functionalization of benzylthioethers catalyzed by Ru/Cu derivatives: synthetic scope and mechanistic possibilities

AuthorsRuiz Morte, Sara ; Villuendas, Pedro ; Urriolabeitia, Esteban P.
Issue Date2016
Citation1st TrapCat (2016)
AbstractThe site-selective activation of C-H bonds promoted by transition metals is currently one of the most powerful tools for the tailored building of complex organic molecules. The selectivity required by the reaction is sometimes achieved according to electronic or steric biases. However, when two or more positions are very similar and their discrimination is not possible, the use of directing groups provides a general solution. Due to this fact hundreds of directing groups are known, almost all of them based on N- and O-bonding atoms. In clear contrast the use of S-directing groups is scarce, in spite of the interest of many S-containing molecules, due to problems related with the deactivation of the catalysts after S-bonding. In this contribution we show that the use of S-directing groups in Ru/Cu catalysis is perfectly compatible. We have studied the coupling of benzylthioethers with internal alkynes, and we found a highly versatile process. By fine tuning of the reaction conditions we have observed either the hydroarylation of the alkyne (only one C-H bond activation, path a) or the oxidative coupling of the arene and the alkyne (double C-H bond activation, path b) affording indene derivatives. On the other hand, when benzylmercaptane is used as starting material, the selective acetoxythiolation of the alkyne is observed (path c). All these results have been rationalized on the basis of the respective reactions mechanisms, which have been fully determined by DFT methods.
DescriptionResumen del trabajo presentado al 1st TransPyrenean Meeting in Catalysis, celebrado en Toulouse (Francia) del 13 al 14 de octubre de 2016.
Appears in Collections:(ISQCH) Comunicaciones congresos
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