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


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Article Info

DATE

2019-12

AUTHORS

Xinyu Zhang, Zhaohong Liu, Xiangyu Yang, Yuanqing Dong, Matteo Virelli, Giuseppe Zanoni, Edward A. Anderson, Xihe Bi

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. More... »

PAGES

284

Identifiers

URI

http://scigraph.springernature.com/pub.10.1038/s41467-018-08253-z

DOI

http://dx.doi.org/10.1038/s41467-018-08253-z

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1111375477

PUBMED

https://www.ncbi.nlm.nih.gov/pubmed/30655536


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Download the RDF metadata as:  json-ld nt turtle xml License info

HOW TO GET THIS DATA PROGRAMMATICALLY:

JSON-LD is a popular format for linked data which is fully compatible with JSON.

curl -H 'Accept: application/ld+json' 'https://scigraph.springernature.com/pub.10.1038/s41467-018-08253-z'

N-Triples is a line-based linked data format ideal for batch operations.

curl -H 'Accept: application/n-triples' 'https://scigraph.springernature.com/pub.10.1038/s41467-018-08253-z'

Turtle is a human-readable linked data format.

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RDF/XML is a standard XML format for linked data.

curl -H 'Accept: application/rdf+xml' 'https://scigraph.springernature.com/pub.10.1038/s41467-018-08253-z'


 

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