Bercaw, John E. and Day, Michael W. and Golisz, Suzanne R. and Hazari, Nilay and Henling, Lawrence M. and Labinger, Jay A. and Schofer, Susan J. and Virgil, Scott (2009) Robotic Lepidoptery: Structural Characterization of (mostly) Unexpected Palladium Complexes Obtained from High-Throughput Catalyst Screening. Organometallics, 28 (17). pp. 5017-5024. ISSN 0276-7333. https://resolver.caltech.edu/CaltechAUTHORS:20090911-153559461
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Abstract
In the course of a high-throughput search for optimal combinations of bidentate ligands with Pd(II) carboxylates to generate oxidation catalysts, we obtained and crystallographically characterized a number of crystalline products. While some combinations afforded the anticipated (L-L)Pd(OC(O)R)_2 structures (L-L = bipyridine, tmeda; R = CH_3, CF_3), many gave unusual oligometallic complexes resulting from reactions such as C−H activation (L-L = sparteine), P−C bond cleavage (L-L = 1,2-bis(diphenylphosphino)ethane, and C−C bond formation between solvent (acetone) and ligand (L-L = 1,4-bis(2,6-diisopropylphenyl)-1,4-diaza-1,3-butadiene). These findings illustrate potential pitfalls of screening procedures based on assuming uniform, in situ catalyst self-assembly.
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| Additional Information: | © 2009 American Chemical Society. Received March 30, 2009. Publication Date (Web): August 20, 2009. The authors acknowledge bp for funding through the MC2 program and thank John C. McKeen of Caltech for TGA and Drs. Thomas J. Crevier and Jeffrey C. Yoder of Symyx for suggestions relating to the robotics experiments. The Bruker KAPPA APEXII X-ray diffractometer was purchased via an NSF CRIF:MU award to the California Institute of Technology, CHE-0639094. Supporting Information: Selected 1H NMR spectra, crystal and refinement data for 5m, selected bond distances of 6, and all CIFs. This material is available free of charge via the Internet at http://pubs.acs.org. CCDC 708866 (1), 713343 (2), 717612 (3), 711734 (4), 717605 (5), 723085 (5m), and 724780 (6) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif. | |||||||||
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| Issue or Number: | 17 | |||||||||
| Record Number: | CaltechAUTHORS:20090911-153559461 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20090911-153559461 | |||||||||
| Official Citation: | Robotic Lepidoptery: Structural Characterization of (mostly) Unexpected Palladium Complexes Obtained from High-Throughput Catalyst Screening John E. Bercaw, Michael W. Day, Suzanne R. Golisz, Nilay Hazari, Lawrence M. Henling, Jay A. Labinger, Susan J. Schofer, Scott Virgil Organometallics 2009 28 (17), 5017-5024 | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 15795 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | George Porter | |||||||||
| Deposited On: | 07 Oct 2009 21:35 | |||||||||
| Last Modified: | 09 Mar 2020 13:19 |
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