1583286-02-5Relevant academic research and scientific papers
INTERMOLECULAR C-H SILYLATION OF UNACTIVATED ARENES
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Paragraph 00111, (2015/03/28)
Reaction mixtures for silvlating arene substrates and methods of using such reaction mixtures to silyiate the arene substrates are provided. Exemplary reaction mixtures include the arene substrate, a liganded metal catalyst, a hydrogen acceptor and an organic solvent. The reaction conditions allow for diverse substituents on the arene substrate.
Iridium-catalyzed silylation of aryl C-H bonds
Cheng, Chen,Hartwig, John F.
supporting information, p. 592 - 595 (2015/01/30)
A method for the iridium-catalyzed silylation of aryl C-H bonds is described. The reaction of HSiMe(OSiMe3)2 with arenes and heteroarenes catalyzed by the combination of [Ir(cod)(OMe)]2 and 2,4,7-trimethylphenanthroline occurs with the aromatic compound as the limiting reagent and with high levels of sterically derived regioselectivity. This new catalytic system occurs with a much higher tolerance for functional groups than the previously reported rhodium-catalyzed silylation of aryl C-H bonds and occurs with a wide range of heteroarenes. The silylarene products are suitable for further transformations, such as oxidation, halogenation, and cross-coupling. Late-stage functionalization of complex pharmaceutical compounds was demonstrated.
Rhodium-catalyzed intermolecular C-H silylation of arenes with high steric regiocontrol
Chen, Cheng,Hartwig, John F.
, p. 853 - 857 (2014/03/21)
Regioselective C-H functionalization of arenes has widespread applications in synthetic chemistry. The regioselectivity of these reactions is often controlled by directing groups or steric hindrance ortho to a potential reaction site. Here, we report a catalytic intermolecular C-H silylation of unactivated arenes that manifests very high regioselectivity through steric effects of substituents meta to a potential site of reactivity. The silyl moiety can be further functionalized under mild conditions but is also inert toward many common organic transformations, rendering the silylarene products useful building blocks. The remote steric effect that we observe results from the steric properties of both the rhodium catalyst and the silane.
