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Mn-Mediated Electrochemical Trifluoromethylation/C(sp^2)–H Functionalization Cascade for the Synthesis of Azaheterocycles

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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/acs.orglett.8b04010DOIArticle
https://pubs.acs.org/doi/suppl/10.1021/acs.orglett.8b04010PublisherSupporting Information
ORCID:
AuthorORCID
Zhang, Lei0000-0001-9031-4318
Liu, Guoquan0000-0003-0680-4811
Yang, Yang0000-0002-4956-2034
Mo, Fanyang0000-0002-4140-3020
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.
Funders:
Funding AgencyGrant Number
National Natural Science Foundation of China21772003
1000 Young Talents ProgramUNSPECIFIED
Peking UniversityUNSPECIFIED
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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