Use of trifluoroacetaldehyde N-tfsylhydrazone as a trifluorodiazoethane surrogate and its synthetic applications

Xinyu Zhang, Zhaohong Liu, Xiangyu Yang, Yuanqing Dong, Matteo Virelli, Giuseppe Zanoni, Edward A. Anderson and Xihe Bi ()
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Xinyu Zhang: Northeast Normal University
Zhaohong Liu: Northeast Normal University
Xiangyu Yang: Northeast Normal University
Yuanqing Dong: Northeast Normal University
Matteo Virelli: University of Pavia
Giuseppe Zanoni: University of Pavia
Edward A. Anderson: University of Oxford
Xihe Bi: Northeast Normal University

Nature Communications, 2019, vol. 10, issue 1, 1-9

Abstract: Abstract Trifluorodiazoethane (CF3CHN2), a highly reactive fluoroalkylating reagent, offers a useful means to introduce trifluoromethyl groups into organic molecules. At present, CF3CHN2 can only be generated by oxidation of trifluoroethylamine hydrochloride under acidic conditions; due to its toxic and explosive nature, its safe generation and use remains a prominent concern, hampering wider synthetic exploitation. Here we report the development of trifluoroacetaldehyde N-tfsylhydrazone (TFHZ-Tfs) as a CF3CHN2 surrogate, which is capable of generating CF3CHN2 in situ under basic conditions. The reaction conditions employed in this chemistry enabled a difluoroalkenylation of X–H bonds (X = N, O, S, Se), affording a wide range of heteroatom-substituted gem-difluoroalkenes, along with Doyle-Kirmse rearrangements and trifluoromethylcyclopropanation reactions, with superior outcomes to approaches using pre-formed CF3CHN2. Given the importance of generally applicable fluorination methodologies, the use of TFHZ-Tfs thus creates opportunities across organic and medicinal chemistry, by enabling the wider exploration of the reactivity of trifluorodiazoethane.

Date: 2019
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DOI: 10.1038/s41467-018-08253-z

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