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A well-defined NHC–Ir(III) catalyst for the silylation of aromatic C–H bonds: substrate survey and mechanistic insights

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Abstract

A well-defined NHC–Ir(III) catalyst, [Ir(H)2(IPr)(py)3][BF4] (IPr = 1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene), that provides access to a wide range of aryl- and heteroaryl-silanes by intermolecular dehydrogenative C–H bond silylation has been prepared and fully characterized. The directed and non-directed functionalisation of C–H bonds has been accomplished successfully using an arene as the limiting reagent and a variety of hydrosilanes in excess, including Et3SiH, Ph2MeSiH, PhMe2SiH, Ph3SiH and (EtO)3SiH. Examples that show unexpected selectivity patterns that stem from the presence of aromatic substituents in hydrosilanes are also presented. The selective bisarylation of bis(hydrosilane)s by directed or non-directed silylation of C–H bonds is also reported herein. Theoretical calculations at the DFT level shed light on the intermediate species in the catalytic cycle and the role played by the ligand system on the Ir(III)/Ir(I) mechanism.

Graphical abstract: A well-defined NHC–Ir(iii) catalyst for the silylation of aromatic C–H bonds: substrate survey and mechanistic insights

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Publication details

The article was received on 04 Nov 2016, accepted on 03 Apr 2017 and first published on 05 Apr 2017


Article type: Edge Article
DOI: 10.1039/C6SC04899D
Citation: Chem. Sci., 2017, Advance Article
  • Open access: Creative Commons BY license
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    A well-defined NHC–Ir(III) catalyst for the silylation of aromatic C–H bonds: substrate survey and mechanistic insights

    L. Rubio-Pérez, M. Iglesias, J. Munárriz, V. Polo, V. Passarelli, J. J. Pérez-Torrente and L. A. Oro, Chem. Sci., 2017, Advance Article , DOI: 10.1039/C6SC04899D

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