Zhang, Zhenxing and Zhang, Lei and Cao, Yang and Li, Feng and Bai, Guangcan and Liu, Guoquan and Yang, Yang and Mo, Fanyang (2019) Mn-Mediated Electrochemical Trifluoromethylation/C(sp^2)–H Functionalization Cascade for the Synthesis of Azaheterocycles. Organic Letters, 21 (3). pp. 762-766. ISSN 1523-7060. https://resolver.caltech.edu/CaltechAUTHORS:20190123-102807445
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Abstract
A general electrohemical strategy for the combined trifluoromethylation/C(sp^2)–H functionalization using Langlois’ reagent as the CF_3 source under oxidant-free conditions was developed. Using Mn salts as the redox mediator, this method provides an efficient and sustainable means to access a variety of functionalized heterocycles bearing a CF_3 moiety. Detailed mechanistic studies are consistent with the formation of CF_3-bound high oxidation state Mn species, suggesting a transition-metal-mediated CF_3 transfer mechanism for this trifluoromethylation/C(sp^2)–H functionalization process.
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| Alternate Title: | Mn-Mediated Electrochemical Trifluoromethylation/C(sp2)–H Functionalization Cascade for the Synthesis of Azaheterocycles | ||||||||||
| Additional Information: | © 2019 American Chemical Society. Received: December 16, 2018; Publication Date (Web): January 23, 2019. Accession Codes: CCDC 1885350 and 1890462 contain the supplementary crystallographic data for this paper. The project was supported by the Natural Science Foundation of China (Grants 21772003). We also thank the “1000-Youth Talents Plan” and Peking University for start-up funds. The authors declare no competing financial interest. | ||||||||||
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| Issue or Number: | 3 | ||||||||||
| Record Number: | CaltechAUTHORS:20190123-102807445 | ||||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20190123-102807445 | ||||||||||
| Official Citation: | Mn-Mediated Electrochemical Trifluoromethylation/C(sp2)–H Functionalization Cascade for the Synthesis of Azaheterocycles. Zhenxing Zhang, Lei Zhang, Yang Cao, Feng Li, Guangcan Bai, Guoquan Liu, Yang Yang, and Fanyang Mo. Organic Letters 2019 21 (3), 762-766. DOI: 10.1021/acs.orglett.8b04010 | ||||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||
| ID Code: | 92424 | ||||||||||
| Collection: | CaltechAUTHORS | ||||||||||
| Deposited By: | Tony Diaz | ||||||||||
| Deposited On: | 23 Jan 2019 18:39 | ||||||||||
| Last Modified: | 03 Oct 2019 20:44 |
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