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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.

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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.

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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
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Issue or Number:14
Record Number:CaltechAUTHORS:20090808-142500065
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Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:14879
Deposited By: George Porter
Deposited On:04 Sep 2009 16:34
Last Modified:03 Oct 2019 00:53

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