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Hoveyda-Grubbs catalyst analogues bearing derivatives of N-phenylpyrrol in carbene ligand - structure, stability, activity and unique ruthenium-phenyl interactions

Abstract

We have synthesized a series of N-phenylpyrrole and N-phenylindole carbenes and used them as ruthenium-ligating moieties in the synthesis of Hoveyda-Grubbs catalysts derivatives. We show that most of these complexes are difficult to synthesize and unstable apart from the N-phenylpyrrole-2,6-diisopropylphenyl ruthenium complex and its perbrominated derivative. These two systems are almost completely inactive in ring-closing metathesis at room temperature and become active only at 80 °C. DFT, SAPT0 and DLPNO-CCSD(T) calculations suggest that the rarely occurring phenyl-ruthenium interactions is responsible for very slow initiation of these precatalysts at low temperatures.

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Publication details

The article was received on 15 Jun 2017, accepted on 09 Aug 2017 and first published on 11 Aug 2017


Article type: Paper
DOI: 10.1039/C7DT02180A
Citation: Dalton Trans., 2017, Accepted Manuscript
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    Hoveyda-Grubbs catalyst analogues bearing derivatives of N-phenylpyrrol in carbene ligand - structure, stability, activity and unique ruthenium-phenyl interactions

    K. Grudzień, B. Trzaskowski, M. Smoleń, R. Gajda, K. Wozniak and K. Grela, Dalton Trans., 2017, Accepted Manuscript , DOI: 10.1039/C7DT02180A

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