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Metal-Free Catalyzed Regioselective Allylic Trifluoromethanesulfonylation of Aromatic Allylic Alcohols with Sodium Trifluoromethanesulfinate
- Source :
- The Journal of Organic Chemistry. 81:1304-1309
- Publication Year :
- 2016
- Publisher :
- American Chemical Society (ACS), 2016.
-
Abstract
- An efficient procedure for the preparation of allylic trifluoromethanesulfones with high regioselectivity from aromatic allylic alcohols/esters and NaSO2CF3 under transition-metal-free conditions is described. A wide range of functional groups were tolerated. This is the first example to realize different types of allylic alcohols, including primary, secondary, and tertiary allylic alcohols, all of which transferred to the corresponding products efficiently in good to excellent yields with readily available and inexpensive NaSO2CF3. The synthetic utility of the method was demonstrated by performing the reaction at gram scale.
- Subjects :
- Allylic rearrangement
Primary (chemistry)
010405 organic chemistry
organic chemicals
Organic Chemistry
food and beverages
Sodium trifluoromethanesulfinate
Regioselectivity
010402 general chemistry
01 natural sciences
0104 chemical sciences
Catalysis
chemistry.chemical_compound
chemistry
Metal free
Organic chemistry
Subjects
Details
- ISSN :
- 15206904 and 00223263
- Volume :
- 81
- Database :
- OpenAIRE
- Journal :
- The Journal of Organic Chemistry
- Accession number :
- edsair.doi.dedup.....2658259f5a6f5e3222f4af04c21169cb
- Full Text :
- https://doi.org/10.1021/acs.joc.5b02674