Microdroplets Catalyze C( sp 2 )–H Nitration Reactions

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Microdroplet chemistry is reforming organic synthesis in a green and sustainable manner in recent years because of the unique catalytic and redox environment at the gas–liquid interface. Nitration, an important way of introducing nitro groups, traditionally requires the use of nitric acid in large amounts under certain catalysts at high temperatures in a long duration. To address these unsustainable problems, we developed a catalyst-free microdroplet method for efficient and mild nitration due to the catalytic activity of the microdroplets. However, catalyst-free microdroplet nitration offered good conversions (maximum 61%) only at the micromolar scale. By externally introducing 1 equiv of TfOH, we achieved 53–98% yields at the molar scale from 11 (hetero)arenes with a 1.06 g h –1 scalability. This method was characterized by short time, high conversion, wide substrate range, and gram ability, making it attractive for nitrated (hetero)arenes.

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