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

Zhan Li, Ke-Feng Wang, Xin Zhao, Huihui Ti, Xu-Ge Liu () and Honggen Wang ()
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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

Nature Communications, 2020, vol. 11, issue 1, 1-12

Abstract: 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.

Date: 2020
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DOI: 10.1038/s41467-020-18834-6

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