Trifluoromethyldiazomethane (CF3CHN2) is an important precursor for introducing trifluoromethyl into organic molecules and is widely used in organic synthetic chemistry. However, there is only one way of producing it, and its storage convenience and use Security has always been a problem that is difficult to solve with traditional methods (see Figure 1).

Figure 1: Problems encountered in the storage and use of trimethyldiazomethane (CF3CHN2)

Trifluoroacetaldehyde N-o-trifluoromethylbenzenesulfonylhydrazone (TFHZ-Tfs) developed by the research group of Professor Bi Xihe from the School of Chemistry of Northeast Normal University is a newly developed trifluoromethyl precursor that fundamentally Addressed its safe use issues.

Solid: easy to store (see Figure 2);
Stable properties and safe operation: TFHZ-Tfs can slowly release trifluoromethyldiazomethane under alkaline conditions, avoiding researchers from contacting and operating dangerous and toxic reagents in experiments;

Wide application range and efficient reaction: TFHZ-Tfs is used in a variety of X-H (X = S, Se, N, O) geminal difluoroalkenylation reactions. This reaction is a heteroatom-substituted geminal difluoroalkenylation reaction that is difficult to synthesize by other methods. Fluoroolefin compounds provide a new synthetic strategy. In addition, the efficient Doyle-Kirmse reaction and cyclopropanation reaction also prove the synthetic efficiency of this new reagent (see Figure 3) [1].

Figure 2: TFHZ-Tfs is a white solid and easy to store

Figure 3:TFHZ-Tfs Efficient application in the geminal difluoroalkylation reaction of X-H Doyle-Kirmse reaction and cyclopropanation reaction

1. Xinyu Zhang, Zhaohong Liu, Xiangyu Yang, Yuanqing Dong, Matteo Virelli, Giuseppe Zanoni, Edward A. Anderson, Xihe Bi. Nat. Commun. 2019, 10, 284

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