Journal
ORGANIC LETTERS
Volume 19, Issue 8, Pages 2106-2109Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b00704
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Funding
- INSA Rouen
- Rouen University
- CNRS
- EFRD
- Labex SynOrg [ANR-11-LABX-0029]
- Region Normandie (Crunch Network)
- China Scholarship Council (CSC)
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A palladium-catalyzed C-H bond functionalization of acrylamides was developed to build up stereoselectively trifluoromethylated 1,3-butadienes. Using a tertiary amide as a directing group, olefins were selectively functionalized with 2-bromo-3,3,3-trifluoropropene to access these important fluorinated compounds. The methodology was extended to the construction of pentafluoroethyl-substituted 1,3-dienes. Mechanistic studies supported by density functional theory calculations suggested a redox neutral mechanism for this transformation.
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