Ritter-type amination of C(sp3)-H bonds enabled by electrochemistry with SO42−

Ling Zhang, Youtian Fu, Yi Shen, Chengyu Liu, Maolin Sun, Ruihua Cheng, Weiping Zhu, Xuhong Qian, Yueyue Ma () and Jinxing Ye ()
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Ling Zhang: East China University of Science and Technology
Youtian Fu: East China University of Science and Technology
Yi Shen: East China University of Science and Technology
Chengyu Liu: East China University of Science and Technology
Maolin Sun: Guangdong University of Technology
Ruihua Cheng: Guangdong University of Technology
Weiping Zhu: East China University of Science and Technology
Xuhong Qian: East China University of Science and Technology
Yueyue Ma: Guangdong University of Technology
Jinxing Ye: East China University of Science and Technology

Nature Communications, 2022, vol. 13, issue 1, 1-8

Abstract: Abstract By merging electricity with sulfate, the Ritter-type amination of C(sp3)-H bonds is developed in an undivided cell under room temperature. This method features broad substrate generality (71 examples, up to 93% yields), high functional-group compatibility, facile scalability, excellent site-selectivity and mild conditions. Common alkanes and electron-deficient alkylbenzenes are viable substrates. It also provides a straightforward protocol for incorporating C-deuterated acetylamino group into C(sp3)-H sites. Application in the synthesis or modification of pharmaceuticals or their derivatives and gram-scale synthesis demonstrate the practicability of this method. Mechanistic experiments show that sulfate radical anion, formed by electrolysis of sulfate, served as hydrogen atom transfer agent to provide alkyl radical intermediate. This method paves a convenient and flexible pathway for realizing various synthetically useful transformations of C(sp3)-H bonds mediated by sulfate radical anion generated via electrochemistry.

Date: 2022
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DOI: 10.1038/s41467-022-31813-3

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