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Chelate-Assisted Ring-Closing Metathesis: A Strategy for Accelerating Macrocyclization at Ambient Temperatures

Carolyn S. Higman, Daniel L. Nascimento, Benjamin J. Ireland, Stephan Audörsch, Gwendolyn A. Bailey, Robert McDonald and Deryn E. Fogg*

*Center for Catalysis Research & Innovation, and Department of Chemistry and Biomolecular Sciences, University of Ottawa, Ottawa, Canada K1N 6N5, Email: dfogguottawa.ca

C. S. Higman, D. L. Nascimento, B. J. Ireland, S. Audörsch, G. A. Bailey, R. McDonald, D. E. Fogg, J. Am. Chem. Soc., 2018, 140, 1604-1607.

DOI: 10.1021/jacs.7b13257 (free Supporting Information)


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Abstract

Incorporation of a hemilabile o-dianiline (ODA) chelate into Ru complexes of N-heterocyclic carbenes accelerates ring-closing metathesis macrocyclization, particularly for dienes bearing polar sites capable of H-bonding. The ligand may also inhibit catalyst decomposition during metathesis.

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Key Words

ring closing metathesis


ID: J48-Y2018