Site-specific Umpolung amidation of carboxylic acids via triplet synergistic catalysis

Yunyun Ning, Shuaishuai Wang, Muzi Li, Jie Han, Chengjian Zhu and Jin Xie ()
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Yunyun Ning: Nanjing University
Shuaishuai Wang: Nanjing University
Muzi Li: Nanjing University
Jie Han: Nanjing University
Chengjian Zhu: Nanjing University
Jin Xie: Nanjing University

Nature Communications, 2021, vol. 12, issue 1, 1-9

Abstract: Abstract Development of catalytic amide bond-forming methods is important because they could potentially address the existing limitations of classical methods using superstoichiometric activating reagents. In this paper, we disclose an Umpolung amidation reaction of carboxylic acids with nitroarenes and nitroalkanes enabled by the triplet synergistic catalysis of FeI2, P(V)/P(III) and photoredox catalysis, which avoids the production of byproducts from stoichiometric coupling reagents. A wide range of carboxylic acids, including aliphatic, aromatic and alkenyl acids participate smoothly in such reactions, generating structurally diverse amides in good yields (86 examples, up to 97% yield). This Umpolung amidation strategy opens a method to address challenging regioselectivity issues between nucleophilic functional groups, and complements the functional group compatibility of the classical amidation protocols. The synthetic robustness of the reaction is demonstrated by late-stage modification of complex molecules and gram-scale applications.

Date: 2021
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DOI: 10.1038/s41467-021-24908-w

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