期刊
JACS AU
卷 2, 期 9, 页码 2152-2161出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacsau.2c00413
关键词
nitration; dinitration; nitrating reagent; nitroaromatics; nitro effect; methyl effect
资金
- National Key Research and Development Program of China [2016YFB0101203]
- Wuhan University
In this study, a powerful nitrating reagent was identified, which enables mild and scalable nitration of various aromatic compounds and allows for selective formation of mononitrated or dinitrated products. This method has important applications in medicinal chemistry.
Nitroaromatics are tremendously valuable organic compounds with a long history of being used as pharmaceuticals, agrochemicals, and explosives as well as vital intermediates to a wide variety of chemicals. Consequently, the exploration of aromatic nitration has become an important endeavor in both academia and industry. Herein, we report the identification of a powerful nitrating reagent, 5-methyl-1,3-dinitro-1H-pyrazole, from the N-nitro-type reagent library constructed using a practical N-H nitration method. This nitrating reagent behaves as a controllable source of the nitronium ion, enabling mild and scalable nitration of a broad range of (hetero)arenes with good functional group tolerance. Of note, our nitration method could be controlled by manipulating the reaction conditions to furnish mononitrated or dinitrated product selectively. The value of this method in medicinal chemistry has been well established by its efficient late-stage C-H nitration of complex biorelevant molecules. Density functional theory (DFT) calculations and preliminary mechanistic studies reveal that the powerfulness and versatility of this nitrating reagent are due to the synergistic nitro effect and methyl effect .
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