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Catalytic Reduction of Alkyl and Aryl Bromides Using Propan-2-ol

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. 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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1002/anie.201708800DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/anie.201708800/abstractPublisherArticle
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
Grubbs, Robert H.0000-0002-0057-7817
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
Funders:
Funding AgencyGrant Number
King Fahd University of Petroleum and Minerals (KFUPM)UNSPECIFIED
Resnick Sustainability InstituteUNSPECIFIED
Subject Keywords:halogens; hydrogen transfer; green chemistry; hydrides; hydrocarbons
Issue or Number:47
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:03 Oct 2019 18:50

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