One-Pot 1,1-Dihydrofluoroalkylation of Amines Using Sulfuryl Fluoride

Sulfuryl fluoride, SO2F2, has been known and used as a fumigant for over 50 years but it has only recently gained widespread interest as a reagent for organic synthesis. Herein we report a novel application of sulfuryl fluoride gas in a new 1,1-dihydrofluoroalkylation reaction, which simply involves...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 140; no. 48; pp. 16464 - 16468
Main Authors Epifanov, Maxim, Foth, Paul J, Gu, Frances, Barrillon, Charlotte, Kanani, Sahil S, Higman, Carolyn S, Hein, Jason E, Sammis, Glenn M
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.12.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
NUCLEOPHILES
TRIFLUOROETHYLATION
ATOMS
OPTIMIZATION
SUFEX
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Summary:Sulfuryl fluoride, SO2F2, has been known and used as a fumigant for over 50 years but it has only recently gained widespread interest as a reagent for organic synthesis. Herein we report a novel application of sulfuryl fluoride gas in a new 1,1-dihydrofluoroalkylation reaction, which simply involves bubbling SO2F2 through a solution of amine, 1,1-dihydrofluoroalcohol, and diisopropylethylamine. The reaction is successful for a wide range of primary and secondary amines, as well as several 1,1-dihydrofluoroalcohols, to afford the 1,1-dihydrofluoroalkylated amines in 42% to 80% isolated yields. The reaction also displays excellent functional group tolerance. The ease of the one-pot activation and alkylation, combined with the wide substrate scope make this new procedure an attractive alternative to existing 1,1-dihydrofluoroalkylation methodologies.
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.8b11309