Haibach, Michael C. and Stoltz, Brian M. and Grubbs, Robert H. (2017) Catalytic Reduction of Alkyl and Aryl Bromides Using Propan-2-ol. Angewandte Chemie International Edition, 56 (47). pp. 15123-15126. ISSN 1433-7851. doi:10.1002/anie.201708800. https://resolver.caltech.edu/CaltechAUTHORS:20171004-144313124
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Abstract
Milstein's complex, (PNN)RuHCl(CO), catalyzes the efficient reduction of aryl and alkyl halides under relatively mild conditions by using propan-2-ol and a base. Sterically hindered tertiary and neopentyl substrates are reduced efficiently, as well as more functionalized aryl and alkyl bromides. The reduction process is proposed to occur by radical abstraction/hydrodehalogenation steps at ruthenium. Our research represents a safer and more sustainable alternative to typical silane, lithium aluminium hydride, and tin-based conditions for these reductions.
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| Alternate Title: | Catalytic Reduction of Alkyl and Aryl Bromides Using Isopropanol | |||||||||
| Additional Information: | © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Manuscript received: August 25, 2017; Accepted manuscript online: October 3, 2017; Version of record online: October 24, 2017. We acknowledge funding from King Fahd University of Petroleum and Minerals. M.C.H. acknowledges funding from the Resnick Sustainability Institute in the form of a postdoctral fellowship. The authors declare no conflict of interest. | |||||||||
| Group: | Resnick Sustainability Institute | |||||||||
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| Subject Keywords: | halogens; hydrogen transfer; green chemistry; hydrides; hydrocarbons | |||||||||
| Issue or Number: | 47 | |||||||||
| DOI: | 10.1002/anie.201708800 | |||||||||
| Record Number: | CaltechAUTHORS:20171004-144313124 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20171004-144313124 | |||||||||
| Official Citation: | M. C. Haibach, B. M. Stoltz, R. H. Grubbs, Angew. Chem. Int. Ed. 2017, 56, 15123. | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 82077 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Tony Diaz | |||||||||
| Deposited On: | 04 Oct 2017 22:03 | |||||||||
| Last Modified: | 15 Nov 2021 19:48 |
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