Amination Utilizing N-Haloimides as Nitrogen Source

doi:10.21127/yaoyigc20210015

Abstract

Abstract: Conventionally, N-bromosuccinimide (NBS) is a brominating and oxidizing reagent in organic synthesis. In our research on N-haloimides in organic transformation, we proposed the concept of utilizing N-haloimides like NBS as an amination reagent, i.e., direct incorporation of imido unit to the target molecules to achieve amination, with the assistance of positive halogen(I). In this paper, we would like to summarize the amination of various fundamental substrates with N-haloimides as the amination reagents. We have developed an N-haloimide-DBU (Lewis base activator) combination system, which affords halogen bonding complex and subsequent ion pair intermediate via halogen transfer. All these reactions feature convenient and readily available reagents, mild conditions, simple execution, broad halogen scope, high efficiency and metal-free. The utilization of N-haloimides as versatile aminating reagents has been demonstrated and further application of the synthetic protocol for the preparation of bioactive and optical materials is expected.

Key words: amination, N-haloimides, halogen activation, nitrogen sources, halogen bond

Hongbo Li, Bao-Yi Ren, and Fu-Shun Liang. Amination Utilizing N-Haloimides as Nitrogen Source[J]. General Chemistry, 2021, 7(4): 210015-210015.

References

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