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Iron-Catalyzed α-Alkylation of Ketones with Secondary Alcohols: Access to β-Disubstituted Carbonyl Compounds
- Source :
- Organic Letters, Organic Letters, American Chemical Society, 2020, 22 (5), pp.2064-2069. ⟨10.1021/acs.orglett.0c00549⟩
- Publication Year :
- 2020
- Publisher :
- HAL CCSD, 2020.
-
Abstract
- An iron-catalyzed borrowing hydrogen strategy has been applied in the synthesis of β-branched carbonyl compounds. Various secondary benzylic and aliphatic alcohols have been used as alkylating reagents under mild reaction conditions. The ketones have been isolated in good to excellent yield. Deuterium labeling experiments provide evidence that the alcohol is the hydride source in this reaction and that no reversible step or hydrogen/deuterium scrambling takes place during the process.
- Subjects :
- Aromatic compounds
Hydrogen
chemistry.chemical_element
Alcohol
Alkylation
010402 general chemistry
01 natural sciences
Biochemistry
Medicinal chemistry
chemistry.chemical_compound
Physical and Theoretical Chemistry
ComputingMilieux_MISCELLANEOUS
010405 organic chemistry
Hydride
[CHIM.ORGA]Chemical Sciences/Organic chemistry
Organic Chemistry
Borrowing hydrogen
[CHIM.CATA]Chemical Sciences/Catalysis
[CHIM.MATE]Chemical Sciences/Material chemistry
Ketones
Hydrocarbons
0104 chemical sciences
chemistry
Deuterium
Reagent
Yield (chemistry)
Alcohols
Post-translational modification
Subjects
Details
- Language :
- English
- ISSN :
- 15237060 and 15237052
- Database :
- OpenAIRE
- Journal :
- Organic Letters, Organic Letters, American Chemical Society, 2020, 22 (5), pp.2064-2069. ⟨10.1021/acs.orglett.0c00549⟩
- Accession number :
- edsair.doi.dedup.....edab2eed34b3eca51eccf7e773513e44