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

Zhang, Jing1; Jiang, Min1; Wang, Chang-Sheng2; Guo, Kai2; Li, Quan-Xin3,4; Ma, Cheng3,4; Ni, Shao-Fei3,4; Chen, Gen-Qiang5,6; Zong, Yan5,6; Lu, Hua1; Xu, Li-Wen1; Shao, Xinxin1

2022-12-27

10.1038/s41467-022-35613-7

NATURE COMMUNICATIONS   Impact Factor & Quartile

2041-1723

["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 S(N)2 substitution of alkyl halides lead to generation of alkenes as major side-products. Thus, formation of a challenging C(sp(3))-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(sp(3))-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.","The pursuit of efficient C-N bond formation is a prime focus of synthetic organic chemistry. Here, the authors documented a base promoted amination between alkyl iodides and diazonium salts via halogen-atom transfer (XAT) process."]

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English

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National Science Foundation of China[22001051] ; Hangzhou Leading Innovation and Entrepreneurship Team Project[TD2020015]

Science & Technology - Other Topics

Multidisciplinary Sciences

WOS:000935585400001

NATURE PORTFOLIO

Web of Science

1.Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Key Lab Organosilicon Chem & Mat Technol, Minist Educ, Hangzhou 311121, Zhejiang, Peoples R China
2.Nanjing Tech Univ, Coll Biotechnol & Pharmaceut Engn, 30 Puzhu Rd S, Nanjing 211816, Peoples R China
3.Shantou Univ, Dept Chem, Shantou 515063, Guangdong, Peoples R China
4.Shantou Univ, Key Lab Preparat & Applicat Ordered Struct Mat Gua, Shantou 515063, Guangdong, Peoples R China
5.Southern Univ Sci & Technol, Acad Adv Interdisciplinary Studies, 1088 Xueyuan Rd, Shenzhen 518055, Peoples R China
6.Southern Univ Sci & Technol, Dept Chem, 1088 Xueyuan Rd, Shenzhen 518055, Peoples R China

Zhang, Jing,Jiang, Min,Wang, Chang-Sheng,et al. Transition-metal free C-N bond formation from alkyl iodides and diazonium salts via halogen-atom transfer[J]. NATURE COMMUNICATIONS,2022,13(1).

Zhang, Jing.,Jiang, Min.,Wang, Chang-Sheng.,Guo, Kai.,Li, Quan-Xin.,...&Shao, Xinxin.(2022).Transition-metal free C-N bond formation from alkyl iodides and diazonium salts via halogen-atom transfer.NATURE COMMUNICATIONS,13(1).

Zhang, Jing,et al."Transition-metal free C-N bond formation from alkyl iodides and diazonium salts via halogen-atom transfer".NATURE COMMUNICATIONS 13.1(2022).