Liang, Yufan and Fu, Gregory C. (2015) Stereoconvergent Negishi Arylations of Racemic Secondary Alkyl Electrophiles: Differentiating between a CF_3 and an Alkyl Group. Journal of the American Chemical Society, 137 (30). pp. 9523-9526. ISSN 0002-7863. PMCID PMC4610818. doi:10.1021/jacs.5b04725. https://resolver.caltech.edu/CaltechAUTHORS:20150728-091314884
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Abstract
In this report, we establish that a readily available nickel/bis(oxazoline) catalyst accomplishes a wide array of enantioconvergent cross-couplings of arylzinc reagents with CF_3-substituted racemic secondary alkyl halides, a process that necessitates that the chiral catalyst be able to effectively distinguish between a CF_3 and an alkyl group in order to provide good ee. We further demonstrate that this method can be applied without modification to the catalytic asymmetric synthesis of other families of fluorinated organic compounds.
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| Additional Information: | © 2015 American Chemical Society. Received: May 6, 2015. Published: July 23, 2015. Support has been provided by the National Institutes of Health (National Institute of General Medical Sciences: R01-GM62871) and the Gordon and Betty Moore Foundation (Caltech Center for Catalysis and Chemical Synthesis). We thank Dr. Allen G. Oliver (University of Notre Dame) and Dr. Nathan D. Schley for assistance. | |||||||||
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| Issue or Number: | 30 | |||||||||
| PubMed Central ID: | PMC4610818 | |||||||||
| DOI: | 10.1021/jacs.5b04725 | |||||||||
| Record Number: | CaltechAUTHORS:20150728-091314884 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20150728-091314884 | |||||||||
| Official Citation: | Stereoconvergent Negishi Arylations of Racemic Secondary Alkyl Electrophiles: Differentiating between a CF3 and an Alkyl Group Yufan Liang and Gregory C. Fu Journal of the American Chemical Society 2015 137 (30), 9523-9526 DOI: 10.1021/jacs.5b04725 | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 59030 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | INVALID USER | |||||||||
| Deposited On: | 28 Jul 2015 18:28 | |||||||||
| Last Modified: | 26 May 2022 16:07 |
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