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Catalytic Dehalogenation of Aryl Chlorides Mediated by Ruthenium(II) Phosphine Complexes

Cucullu, Michèle E. and Nolan, Steven P. and Belderrain, Tomàs R. and Grubbs, Robert H. (1999) Catalytic Dehalogenation of Aryl Chlorides Mediated by Ruthenium(II) Phosphine Complexes. Organometallics, 18 (7). pp. 1299-1304. ISSN 0276-7333. https://resolver.caltech.edu/CaltechAUTHORS:20180518-152454626

[img] PDF (Figures giving plots of the conversion of chlorobenzene to benzene vs reaction temperature using in situ generated catalyst without dihydrogen and of the reaction kinetics at 80 °C for dehalogenation of chlorobenzene to benzene) - Supplemental Material
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Abstract

The catalytic dechlorination of aryl chlorides performed by RuHCl(H_2)_2(PCy_3)_2 and RuH_2(H_2)_2(PCy_3)_2 in alcohols is rapid and complete within 1 h. The mechanism involves a transfer hydrogenation step with participation of the alcohol. The system exhibits significant functional group tolerance. The catalyst can be generated in situ from [RuCl_2(COD)]_x (COD = cyclooctadiene) and 2 equiv of phosphine (PCy_3 or P^iPr_3). Catalytic conversions are similar to those observed when an isolated precatalyst is used. Mechanistic considerations and the scope of the process are discussed.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://dx.doi.org/10.1021/om980682nDOIArticle
https://pubs.acs.org/doi/suppl/10.1021/om980682nPublisherSupporting Information
ORCID:
AuthorORCID
Grubbs, Robert H.0000-0002-0057-7817
Additional Information:© 1999 American Chemical Society. Received August 11, 1998. The National Science Foundation is gratefully acknowledged for support of this work.
Funders:
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Issue or Number:7
Record Number:CaltechAUTHORS:20180518-152454626
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20180518-152454626
Official Citation:Catalytic Dehalogenation of Aryl Chlorides Mediated by Ruthenium(II) Phosphine Complexes Michèle E. Cucullu, Steven P. Nolan, Tomás R. Belderrain, and Robert H. Grubbs Organometallics 1999 18 (7), 1299-1304 DOI: 10.1021/om980682n
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:86471
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:21 May 2018 15:31
Last Modified:03 Oct 2019 19:44

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