2022

2022-01- Synthesis and further use of SF5-alkynes as platforms for the design of more complex SF5-containing products

Popek, L.; Nguyen, T. M.; Blanchard, N.; Cahard, D.; Bizet V. Tetrahedron, 2022, 117-118, 132814.

Pentafluorosulfanyl group is known as an emerging fluorinated group, it has been reported for the first time in 1960, and then remained an exotic fluorinated group for years, but nowadays this group is rising in interest and many groups and companies start to investigate this fluorinated motif in more depth. Indeed, SF5 is known as a “super CF3”, gathering and magnifying the benefits of CF3 that are a large volume, a high electronegativity and a high lipophilicity, which are highly valuable properties for drugs development. In parallel, a few applications of SF5-containing molecules has begun to appear in materials science, drug design or crop protection, but innovation remains highly dependent on the synthetic methods available to introduce SF5 in organic molecules. In this report, we turned our attention more specifically to SF5-alkynes, from their synthesis to applications.

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2022-02- Radical Cyclization of Ynamides to Nitrogen Heterocycles

Zhang, C.; Blanchard, N.; Evano G. Synthesis, 2022, in press, DOI: 10.1055/a-1868-8092.

An efficient radical cyclization of suitably functionalized ynamides to nitrogen-containing heterocycles is reported. Upon reaction with tributyltin hydride in the presence of catalytic amounts of AIBN in toluene at 80 °C, a range of ynamides bearing a N-iodopropyl chain could be smoothly cyclized, in a highly regio- and stereo- selective manner, to the corresponding 2-arylidene-pyrrolidines in good to excellent yields. The exocyclic double bond was in addition shown to be an excellent anchor for further chemical diversification and the generality of this radical cyclization could be highlighted by its extension to the synthesis of other nitrogen heterocycles including piperidines, azepanes, pyrazolidines and hexahydropyridazines.

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