Stereoselective Synthesis of (Z)‐β‐Enamido Triflates and Fluorosulfonates from N‐Fluoroalkylated Triazoles

N‐Fluoroalkylated 1,2,3‐triazoles in the presence of triflic acid or fluorosulfonic acid underwent a cascade reaction consisting of triazole protonation, ring opening, nitrogen elimination, sulfonate addition, HF elimination, and hydrolysis to furnish novel trifluoromethanesulfonyloxy‐ or fluorosulf...

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Bibliographic Details
Published in:Chemistry : a European journal 2019-06, Vol.25 (32), p.7640-7644
Main Authors: Markos, Athanasios, Voltrová, Svatava, Motornov, Vladimir, Tichý, David, Klepetářová, Blanka, Beier, Petr
Format: Article
Language:English
Subjects:
1,2,3-triazoles
Cascade chemical reactions
Cations
Chemical reactions
Chemistry
enamides
Nitrogen
Oxazoles
Protonation
Ring opening
Stereoselectivity
Substitutes
Triazoles
triazolium salts
Triflic acid
vinyl cations
vinyl triflates
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Summary:N‐Fluoroalkylated 1,2,3‐triazoles in the presence of triflic acid or fluorosulfonic acid underwent a cascade reaction consisting of triazole protonation, ring opening, nitrogen elimination, sulfonate addition, HF elimination, and hydrolysis to furnish novel trifluoromethanesulfonyloxy‐ or fluorosulfonyloxy‐substituted enamides, respectively, in a highly stereoselective fashion. The vinyl triflates underwent cross‐coupling reactions to a variety of substituted enamides and serve as sources of the aminovinyl cations. In reactions with triflic acid, electron‐rich triazoles afforded 2‐fluoroalkylated oxazoles. Transformation of N‐fluoroalkylated 1,2,3‐triazoles in the presence of triflic or fluorosulfonic acids is presented. These compounds are converted into trifluoromethanesulfonyloxy‐ or fluorosulfonyloxy‐substituted enamides in a highly stereoselective fashion. The trifluoromethanesulfonyl enamides are competent partners for cross‐coupling reactions to stereodefined enamides (see scheme).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201901632