Transition-metal free C–N bond formation from alkyl iodides and diazonium salts via halogen-atom transfer

Jing Zhang, Min Jiang, Chang-Sheng Wang (), Kai Guo (), Quan-Xin Li, Cheng Ma, Shao-Fei Ni, Gen-Qiang Chen, Yan Zong, Hua Lu (), Li-Wen Xu and Xinxin Shao ()
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Jing Zhang: Hangzhou Normal University
Min Jiang: Hangzhou Normal University
Chang-Sheng Wang: Nanjing Tech University
Kai Guo: Nanjing Tech University
Quan-Xin Li: Shantou University
Cheng Ma: Shantou University
Shao-Fei Ni: Shantou University
Gen-Qiang Chen: Southern University of Science and Technology
Yan Zong: Southern University of Science and Technology
Hua Lu: Hangzhou Normal University
Li-Wen Xu: Hangzhou Normal University
Xinxin Shao: Hangzhou Normal University

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

Abstract: Abstract Construction of C-N bond continues to be one part of the most significant goals in organic chemistry because of the universal applications of amines in pharmaceuticals, materials and agrochemicals. However, E2 elimination through classic SN2 substitution of alkyl halides lead to generation of alkenes as major side-products. Thus, formation of a challenging C(sp3)-N bond especially on tertiary carbon center remains highly desirable. Herein, we present a practical alternative to prepare primary, secondary and tertiary alkyl amines with high efficiency between alkyl iodides and easily accessible diazonium salts. This robust transformation only employs Cs2CO3 promoting halogen-atom transfer (XAT) process under transition-metal-free reaction conditions, thus providing a rapid method to assemble diverse C(sp3)-N bonds. Moreover, diazonium salts served as alkyl radical initiator and amination reagent in the reaction. Mechanism studies suggest this reaction undergo through halogen-atom transfer process to generate active alkyl radical which couples with diazonium cations to furnish final products.

Date: 2022
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DOI: 10.1038/s41467-022-35613-7

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