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Competitive Activation of a Methyl C−H Bond of Dimethylformamide at an Iridium Center

Scott, Valerie J. and Henling, Lawrence M. and Day, Michael W. and Bercaw, John E. and Labinger, Jay A. (2009) Competitive Activation of a Methyl C−H Bond of Dimethylformamide at an Iridium Center. Organometallics, 28 (14). pp. 4229-4230. ISSN 0276-7333. http://resolver.caltech.edu/CaltechAUTHORS:20090808-142500065

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Abstract

During the synthesis of [AsPh_4][Ir(CO)_2I_3Me] by refluxing IrCl_3·3H_2O in DMF (DMF = dimethylformamide) in the presence of aqueous HCl, followed by sequential treatment with [AsPh_4]Cl, NaI, and methyl iodide and finally recrystallization from methylene chloride/pentane, three crystalline byproducts were obtained: [AsPh4]_2[Ir(CO)I_5], [AsPh_4]_2[trans-Ir(CO)I_4Cl], and [AsPh_4][Ir(CO)(κ^2O,C-CH_2NMeCHO)Cl_2I]. The last of these, whose structure (along with the others) was determined by X-ray diffraction, results from activation of a methyl C−H bond of dimethylformamide, rather than the normally much more reactive aldehydic C−H bond.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/om9002413DOIArticle
http://pubs.acs.org/doi/abs/10.1021/om900241313PublisherArticle
ORCID:
AuthorORCID
Labinger, Jay A.0000-0002-1942-9232
Additional Information:Copyright © 2009 American Chemical Society. Received March 30, 2009. Publication Date (Web): May 28, 2009. We wish to thank Dr. Nilay Hazari for useful discussions. This work was supported by BP through the MC2 program. The Bruker KAPPA APEXII X-ray diffractometer was purchased via an NSF CRIF:MU award to the California Institute of Technology (No. CHE-0639094). Supporting Information A CIF file giving crystallographic data for 6. This material is available free of charge via the Internet at http://pubs.acs.org.
Funders:
Funding AgencyGrant Number
BP MC2 programUNSPECIFIED
NSFCHE-0639094
Issue or Number:14
Record Number:CaltechAUTHORS:20090808-142500065
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20090808-142500065
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:14879
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:04 Sep 2009 16:34
Last Modified:20 Sep 2017 23:04

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