942206-10-2Relevant academic research and scientific papers
SuFEx-enabled, chemoselective synthesis of triflates, triflamides and triflimidates
Alonso, Mercedes,De Borggraeve, Wim M.,Demaerel, Joachim,Hoppenbrouwers, Fien,Li, Bing-Yu,Van Lommel, Ruben,Verhelst, Steven H. L.,Voets, Lauren
, p. 2270 - 2279 (2022/03/08)
Sulfur(vi) Fluoride Exchange (SuFEx) chemistry has emerged as a next-generation click reaction, designed to assemble functional molecules quickly and modularly. Here, we report the ex situ generation of trifluoromethanesulfonyl fluoride (CF3SO2F) gas in a two chamber system, and its use as a new SuFEx handle to efficiently synthesize triflates and triflamides. This broadly tolerated protocol lends itself to peptide modification or to telescoping into coupling reactions. Moreover, redesigning the SVI-F connector with a SO → SNR replacement furnished the analogous triflimidoyl fluorides as SuFEx electrophiles, which were engaged in the synthesis of rarely reported triflimidate esters. Notably, experiments showed H2O to be the key towards achieving chemoselective trifluoromethanesulfonation of phenols vs. amine groups, a phenomenon best explained - using ab initio metadynamics simulations - by a hydrogen bonded termolecular transition state for the CF3SO2F triflylation of amines. This journal is
A general synthesis of halo-oligopyridines. The Garlanding concept
Voisin-Chiret, Anne Sophie,Bouillon, Alexandre,Burzicki, Grégory,Célant, Melanie,Legay, Rémi,El-Kashef, Hussein,Rault, Sylvain
experimental part, p. 607 - 612 (2009/04/06)
This paper sets forth a global synthetic strategy based on the Garlanding concept to design and to produce halo-oligopyridines. This strategy allows to prepare an infinite number of these new compounds and hence to create a library of halo-oligopyridines.
