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Issue 35, 2017
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Hoveyda–Grubbs catalyst analogues bearing the derivatives of N-phenylpyrrol in the carbene ligand – structure, stability, activity and unique ruthenium–phenyl interactions

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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 catalyst 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 are responsible for the very slow initiation of these precatalysts at low temperatures.

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

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Article information


Submitted
15 Jun 2017
Accepted
09 Aug 2017
First published
11 Aug 2017

Dalton Trans., 2017,46, 11790-11799
Article type
Paper

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

K. Grudzień, B. Trzaskowski, M. Smoleń, R. Gajda, K. Woźniak and K. Grela, Dalton Trans., 2017, 46, 11790
DOI: 10.1039/C7DT02180A

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