Unveiling the Use of 1,1-Bis(triflyl)ethylene as CF3SO2CHCH2 Source with the Assistance of (n‑Bu)4NF: Synthesis of 3‑[(Trifluoromethyl)sulfonyl]cyclobut-1-enes

Unveiling the Use of 1,1-Bis(triflyl)ethylene as CF3SO2CHCH2 Source with the Assistance of (n‑Bu)4NF: Synthesis of 3‑[(Trifluoromethyl)sulfonyl]cyclobut-1-enes

Allylic sulfone-embedded cyclobutenes have been prepared in one pot from alkynes. The carbocycle and the alkenyl sulfone moieties were installed through consecutive bis­(triflyl)­cyclobutenylation of a triple bond and tetra-n-butylammonium fluoride (TBAF)-assisted hydrodesulfonylation of an allylic...

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Veröffentlicht in:Organic letters 2024-05, Vol.26 (21), p.4560-4565
Hauptverfasser: Petcu, A. Sonia, Lázaro-Milla, Carlos, Alonso, José M., Almendros, Pedro
Format: Artikel
Sprache:eng
Schlagworte:
alkynes
fluorides
Letter
moieties
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Zusammenfassung:Allylic sulfone-embedded cyclobutenes have been prepared in one pot from alkynes. The carbocycle and the alkenyl sulfone moieties were installed through consecutive bis­(triflyl)­cyclobutenylation of a triple bond and tetra-n-butylammonium fluoride (TBAF)-assisted hydrodesulfonylation of an allylic bis­(sulfone). It is noteworthy that 1,1-bis­(triflyl)­ethylene acts as a CF3SO2CHCH2 source for the first time.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c01514