Syntheses of Trifluoroethylated N-Heterocycles from Vinyl Azides and Togni’s Reagent Involving 1,n-Hydrogen-Atom Transfer Reactions
Terhorst, S., Prakash Tiwari, D., Meister, D., Petran, B., Rissanen, K., & Bolm, C. (2020). Syntheses of Trifluoroethylated N-Heterocycles from Vinyl Azides and Togni’s Reagent Involving 1,n-Hydrogen-Atom Transfer Reactions. Organic Letters, 22(12), 4766-4770. https://doi.org/10.1021/acs.orglett.0c01566
Published inOrganic Letters
© 2020 American Chemical Society
2,2,2-Trifluoroethyl-substituted 3-oxazolines, 3-thiazolines, and 5,6-dihydro-2H-1,3-oxazines have been obtained by reacting substituted vinyl azides with a combination of Togni’s reagent and substoichiometric amounts of iron(II) chloride. The results of density functional theory calculations support the proposed mechanism involving 1,n-hydrogen-atom transfer reactions.
PublisherAmerican Chemical Society
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Additional information about fundingThe authors are grateful to the Alexander von Humboldt Foundation for support of K.R. (AvH research award) and D.P.T. (AvH postdoctoral fellowship). The simulations were performed with computing resources granted by RWTH Aachen University under Project rwth0354.
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