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Deoxygenative alkylation of tertiary amides using alkyl iodides under visible light

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Abstract

It is an unceasing goal for organic chemists to develop new catalytic methodologies for functional group transformations of widespread molecular structures. Amides are readily available from simple and reliable reactions, which are common structural units found in biologically active compounds. Consequently, they are attractive to be exploited in amine synthesis by reductive cross coupling. However, deoxygenative functionalization of amides is a long-standing challenge owing to the inertness of the resonance-stabilized amide C=O bond. In this work, a deoxygenative alkylation strategy was demonstrated, which combines amides and alkyl iodides to build structurally diverse tertiary alkylamines in a single step. Compared with previous deoxygenative alkylation of amides using organometallic reagents as functional partner, this work uses stable and easily available alkyl halides as functionalization reagents. The versatile and flexible strategy plus structural and functional diversity of readily available amides and alkyl iodides renders it highly appealing for the streamlined synthesis of tertiary amines and would be of much interest in areas such as pharmaceutical and agrochemical research.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (22171278, 21821002).

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Author notes

  1. These authors contributed equally to this work.

Authors and Affiliations

  1. The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Laboratory of Rare Earth Functional Materials, College of Chemistry and Materials Science, Shanghai Normal University, Shanghai, 200234, China

    Feng Zhao

  2. State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China

    Feng Zhao, Feng Jiang & Xiaoming Wang

  3. School of Chemistry and Materials Science, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou, 310024, China

    Feng Jiang & Xiaoming Wang

Authors
  1. Feng Zhao
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  2. Feng Jiang
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  3. Xiaoming Wang
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Correspondence to Xiaoming Wang.

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Conflict of interest The authors declare no conflict of interest.

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Supporting information The supporting information is available online at http://chem.scichina.com and http://link.springer.com/journal/11426. The supporting materials are published as submitted, without typesetting or editing. The responsibility for scientific accuracy and content remains entirely with the authors.

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Zhao, F., Jiang, F. & Wang, X. Deoxygenative alkylation of tertiary amides using alkyl iodides under visible light. Sci. China Chem. 65, 2231–2237 (2022). https://doi.org/10.1007/s11426-022-1331-y

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  • DOI: https://doi.org/10.1007/s11426-022-1331-y

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