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Manganese-mediated reductive functionalization of activated aliphatic acids and primary amines

Author

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  • Zhan Li

    (Sun Yat-sen University)

  • Ke-Feng Wang

    (Guangzhou Medical University)

  • Xin Zhao

    (Guangzhou Medical University)

  • Huihui Ti

    (Guangzhou Medical University)

  • Xu-Ge Liu

    (Sun Yat-sen University)

  • Honggen Wang

    (Sun Yat-sen University)

Abstract

Alkyl carboxylic acids as well as primary amines are ubiquitous in all facets of biological science, pharmaceutical science, chemical science and materials science. By chemical conversion to redox-active esters (RAE) and Katritzky’s N-alkylpyridinium salts, respectively, alkyl carboxylic acids and primary amines serve as ideal starting materials to forge new connections. In this work, a Mn-mediated reductive decarboxylative/deaminative functionalization of activated aliphatic acids and primary amines is disclosed. A series of C-X (X = S, Se, Te, H, P) and C-C bonds are efficiently constructed under simple and mild reaction conditions. The protocol is applicable to the late-stage modification of some structurally complex natural products or drugs. Preliminary mechanistic studies suggest the involvement of radicals in the reaction pathway.

Suggested Citation

  • Zhan Li & Ke-Feng Wang & Xin Zhao & Huihui Ti & Xu-Ge Liu & Honggen Wang, 2020. "Manganese-mediated reductive functionalization of activated aliphatic acids and primary amines," Nature Communications, Nature, vol. 11(1), pages 1-12, December.
    • Handle: RePEc:nat:natcom:v:11:y:2020:i:1:d:10.1038_s41467-020-18834-6
    DOI: 10.1038/s41467-020-18834-6
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