Decarboxylative tandem C-N coupling with nitroarenes via SH2 mechanism

Shuaishuai Wang, Tingrui Li, Chengyihan Gu, Jie Han, Chuan-Gang Zhao, Chengjian Zhu (), Hairen Tan and Jin Xie ()
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Shuaishuai Wang: School of Chemistry and Chemical Engineering, Nanjing University
Tingrui Li: School of Chemistry and Chemical Engineering, Nanjing University
Chengyihan Gu: School of Chemistry and Chemical Engineering, Nanjing University
Jie Han: School of Chemistry and Chemical Engineering, Nanjing University
Chuan-Gang Zhao: School of Chemistry and Chemical Engineering, Nanjing University
Chengjian Zhu: School of Chemistry and Chemical Engineering, Nanjing University
Hairen Tan: College of Engineering and Applied Sciences, Nanjing University
Jin Xie: School of Chemistry and Chemical Engineering, Nanjing University

Nature Communications, 2022, vol. 13, issue 1, 1-10

Abstract: Abstract Aromatic tertiary amines are one of the most important classes of organic compounds in organic chemistry and drug discovery. It is difficult to efficiently construct tertiary amines from primary amines via classical nucleophilic substitution due to consecutive overalkylation. In this paper, we have developed a radical tandem C-N coupling strategy to efficiently construct aromatic tertiary amines from commercially available carboxylic acids and nitroarenes. A variety of aromatic tertiary amines can be furnished in good yields (up to 98%) with excellent functional group compatibility under mild reaction conditions. The use of two different carboxylic acids also allows for the concise synthesis of nonsymmetric aromatic tertiary amines in satisfactory yields. Mechanistic studies suggest the intermediacy of the arylamine–(TPP)Fe(III) species and might provide a possible evidence for an SH2 (bimolecular homolytic substitution) pathway in the critical C-N bond formation step.

Date: 2022
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DOI: 10.1038/s41467-022-30176-z

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